Use of amines in heavy oil transport

ABSTRACT

Provided herein are, inter alia, heavy crude oil emulsion compositions and methods of making the same. The compositions and methods provided herein are particularly useful for the transport of heavy crude oils.

CROSS-REFERENCE TO RELATED APPLICATIONS

This application claims the benefit of U.S. Provisional Application No.61/815,579 filed Apr. 24, 2013, which is hereby incorporated in itsentirety and for all purposes.

BACKGROUND OF THE INVENTION

Heavy crude oils are defined as oils having an API (American PetroleumIndustry) gravity of less than 20, and are viscous at lower temperatureswhen produced from a reservoir. The viscous heavy crude oils aredifficult to transport in pipelines especially at low temperature. Theviscosity of heavy crude oils at low temperature can be millions of cp.Methods used to lower the viscosity of heavy crude oils to facilitatetheir transport include, for example, expensive procedures involvingheating the oil to a high temperature (e.g. 100° C.) before, and perhapsduring the transport in a vessel (e.g. pipeline). Prior attempts to formlow viscosity emulsions of heavy crude oils have had limited success inpart due to difficulties in maintaining and controlling such emulsion,especially at ambient temperatures and during transport.

Therefore there is a need in the art for cost effective compositions andmethods of transporting heavy crude oils at lower temperatures afterthey have been extracted from a reservoir or storage. Provided hereinare methods and compositions addressing these and other needs in theart.

BRIEF SUMMARY OF THE INVENTION

Provided herein, inter alia, are heavy crude oil emulsion compositionsincluding a heavy crude oil, a co-solvent and water and havingsurprisingly low viscosities at low water content. Due to their lowviscosity, the emulsion compositions provided herein are particularlyuseful as a means for transporting heavy crude oils at ambienttemperatures. Compared to existing transport techniques used in the art,the present emulsion compositions are highly versatile, stable and costeffective.

In one aspect, a heavy crude oil emulsion is provided. The heavy crudeoil emulsion includes a heavy crude oil, water and a co-solvent. Theco-solvent is an alkylamine or a compound having the formula:

In formula (I) R^(1A) and R^(1B) are independently hydrogen,unsubstituted C₁-C₈ alkyl, unsubstituted cycloalkyl, unsubstitutedheterocycloalkyl, unsubstituted aryl, unsubstituted heteroaryl, C₁-C₆alkylamine or

R² and R³ are independently hydrogen or unsubstituted C₁-C₂ alkyl. Thesymbol n is an integer from 1 to 30. The symbol m is an integer from 1to 30 and the heavy crude oil emulsion is within a transport vessel.

In another aspect, a method of forming a heavy crude oil emulsion isprovided. The method includes contacting a heavy crude oil extractedfrom an oil reservoir with a co-solvent and water at an emulsion formingtemperature, thereby forming a high temperature heavy crude oilemulsion. The high temperature heavy crude oil emulsion is allowed tocool to a transport temperature, thereby forming a heavy crude oilemulsion. The co-solvent is an alkylamine or a compound having theformula:

In formula (I) R^(1A) and R^(1B) are independently hydrogen,unsubstituted C₁-C₈ alkyl, unsubstituted cycloalkyl, unsubstitutedheterocycloalkyl, unsubstituted aryl, unsubstituted heteroaryl, C₁-C₆alkylamine or

R² and R³ are independently hydrogen or unsubstituted C₁-C₂ alkyl. Thesymbol n is an integer from 1 to 30, and m is an integer from 1 to 30.

In another aspect, a method of optimizing a heavy crude oil emulsion isprovided. The method includes contacting a plurality of heavy crude oilsamples extracted from an oil reservoir with an amount of a co-solvent,an amount of a salt and an amount of water at an emulsion formingtemperature, wherein the amount of a co-solvent, the amount of a saltand the amount of water is different for each of the plurality of heavycrude oil samples, thereby forming a plurality of different hightemperature heavy crude oil emulsion samples. The plurality of differenthigh temperature heavy crude oil emulsion samples is allowed to cool toan ambient temperature, thereby forming a plurality of different lowtemperature heavy crude oil emulsion samples. A low temperature heavycrude oil emulsion sample is identified amongst the plurality ofdifferent low temperature heavy crude oil emulsion samples having aviscosity at least 100 times lower than the viscosity of the heavy crudeoil, thereby optimizing a heavy crude oil emulsion. The co-solvent is analkylamine or a compound having the formula:

In formula (I) R^(1A) and R^(1B) are independently hydrogen,unsubstituted C₁-C₈ alkyl, unsubstituted cycloalkyl, unsubstitutedheterocycloalkyl, unsubstituted aryl, unsubstituted heteroaryl, C₁-C₆alkylamine or

R² and R³ are independently hydrogen or unsubstituted C₁-C₂ alkyl. Thesymbol n is an integer from 1 to 30, and m is an integer from 1 to 30.

In another aspect, a method of transporting a heavy crude oil isprovided. The method includes extracting a heavy crude oil from an oilreservoir, thereby forming an extracted heavy crude oil. The extractedheavy crude oil is contacted with a co-solvent and water at an emulsionforming temperature, thereby forming a high temperature heavy crude oilemulsion. The high temperature heavy crude oil emulsion is allowed tocool to a transport temperature, thereby forming a heavy crude oilemulsion. The heavy crude oil emulsion is transported from a firstlocation to a second location, thereby transporting the heavy crude oil.The co-solvent is an alkylamine or a compound having the formula:

In formula (I) R^(1A) and R^(1B) are independently hydrogen,unsubstituted C₁-C₈ alkyl, unsubstituted cycloalkyl, unsubstitutedheterocycloalkyl, unsubstituted aryl, unsubstituted heteroaryl, C₁-C₆alkylamine or

R² and R³ are independently hydrogen or unsubstituted C₁-C₂ alkyl. Thesymbol n is an integer from 1 to 30 and m is an integer from 1 to 30.

In another aspect, a method of forming a heavy crude oil emulsion in aproduction well is provided. The method includes contacting an extractedheavy crude oil in a production well with a co-solvent and water,thereby forming a heavy crude oil emulsion in the production well. Theco-solvent is an alkylamine or a compound having the formula:

In formula (I) R^(1A) and R^(1B) are independently hydrogen,unsubstituted C₁-C₈ alkyl, unsubstituted cycloalkyl, unsubstitutedheterocycloalkyl, unsubstituted aryl, unsubstituted heteroaryl, C₁-C₆alkylamine or

R² and R³ are independently hydrogen or unsubstituted C₁-C₂ alkyl, n isan integer from 1 to 30 and m is an integer from 1 to 30.

In another aspect, a method of transporting an extracted heavy crude oilfrom a production well is provided. The method includes contacting anextracted heavy crude oil in a production well with a co-solvent, andwater at an emulsion forming temperature, thereby forming a heavy crudeoil emulsion in a production well. The heavy crude oil emulsion istransported from the production well to the surface, therebytransporting the extracted heavy crude oil from the production well. Theco-solvent is an alkylamine or a compound having the formula:

In formula (I) R^(1A) and R^(1B) are independently hydrogen,unsubstituted C₁-C₈ alkyl, unsubstituted cycloalkyl, unsubstitutedheterocycloalkyl, unsubstituted aryl, unsubstituted heteroaryl, C₁-C₆alkylamine or

R² and R³ are independently hydrogen or unsubstituted C₁-C₂ alkyl, n isan integer from 1 to 30 and m is an integer from 1 to 30.

In another aspect, a heavy crude oil emulsion is provided. The heavycrude oil emulsion includes an amphiphilic co-solvent, a first phase anda second phase, wherein the first phase includes an oil-immisciblecompound and the second phase includes a heavy crude oil. Theamphiphilic co-solvent is an alkylamine or a compound having theformula:

In formula (I) R^(1A) and R^(1B) are independently hydrogen,unsubstituted C₁-C₈ alkyl, unsubstituted cycloalkyl, unsubstitutedheterocycloalkyl, unsubstituted aryl, unsubstituted heteroaryl, C₁-C₆alkylamine or

R² and R³ are independently hydrogen or unsubstituted C₁-C₂ alkyl, n isan integer from 1 to 30 and m is an integer from 1 to 30.

In another aspect, a heavy crude oil emulsion is provided. The heavycrude oil emulsion includes a first phase and a second phase, whereinthe first phase includes an oil-immiscible compound and the second phaseincludes a heavy crude oil.

In another aspect, a method of forming a heavy crude oil emulsion isprovided. The method includes contacting a heavy crude oil extractedfrom an oil reservoir with an oil-immiscible compound and an amphiphilicco-solvent at an emulsion forming temperature, thereby forming a hightemperature heavy crude oil emulsion. The high temperature heavy crudeoil emulsion is allowed to cool to a transport temperature, therebyforming a heavy crude oil emulsion. The amphiphilic co-solvent is analkylamine or a compound having the formula:

In formula (I) R^(1A) and R^(1B) are independently hydrogen,unsubstituted C₁-C₈ alkyl, unsubstituted cycloalkyl, unsubstitutedheterocycloalkyl, unsubstituted aryl, unsubstituted heteroaryl, C₁-C₆alkylamine or

R² and R³ are independently hydrogen or unsubstituted C₁-C₂ alkyl, n isan integer from 1 to 30 and m is an integer from 1 to 30.

In another aspect, a method of forming a heavy crude oil emulsion in aproduction well is provided. The method includes contacting an extractedheavy crude oil in a production well with an oil-immiscible compound andan amphiphilic co-solvent, thereby forming a heavy crude oil emulsion ina production well. The amphiphilic co-solvent is an alkylamine or acompound having the formula:

In formula (I) R^(1A) and R^(1B) are independently hydrogen,unsubstituted C₁-C₈ alkyl, unsubstituted cycloalkyl, unsubstitutedheterocycloalkyl, unsubstituted aryl, unsubstituted heteroaryl, C₁-C₆alkylamine or

R² and R³ are independently hydrogen or unsubstituted C₁-C₂ alkyl, n isan integer from 1 to 30 and m is an integer from 1 to 30.

In another aspect, a method of transporting an extracted heavy crude oilfrom a production well is provided. The method includes contacting anextracted heavy crude oil in a production well with an oil-immisciblecompound and an amphiphilic co-solvent at an emulsion formingtemperature, thereby forming a heavy crude oil emulsion in a productionwell. The heavy crude oil emulsion is transported from the productionwell to the surface, thereby transporting the extracted heavy crude oilfrom the production well. The amphiphilic co-solvent is an alkylamine ora compound having the formula:

In formula (I) R^(1A) and R^(1B) are independently hydrogen,unsubstituted C₁-C₈ alkyl, unsubstituted cycloalkyl, unsubstitutedheterocycloalkyl, unsubstituted aryl, unsubstituted heteroaryl, C₁-C₆alkylamine or

R² and R³ are independently hydrogen or unsubstituted C₁-C₂ alkyl, n isan integer from 1 to 30 and m is an integer from 1 to 30.

In another aspect, a non-aqueous composition including an oil-immisciblecompound and an amphiphilic co-solvent is provided. The amphiphilicco-solvent is an alkylamine or a compound having the formula:

In formula (I) R^(1A) and R^(1B) are independently hydrogen,unsubstituted C₁-C₈ alkyl, unsubstituted cycloalkyl, unsubstitutedheterocycloalkyl, unsubstituted aryl, unsubstituted heteroaryl, C₁-C₆alkylamine or

R² and R³ are independently hydrogen or unsubstituted C₁-C₂ alkyl, n isan integer from 1 to 30 and m is an integer from 1 to 30.

BRIEF DESCRIPTION OF THE DRAWINGS

FIG. 1: shows the effect of temperature on the viscosity of four heavycrude oils mentioned in table 3. Power law model was found to bestdescribe the relationship of heavy oil viscosity vs. temperature. Themeasurements were taken using an ARES rheometer.

FIG. 2: Apparent viscosity of oil 85% A emulsions vs. shear rate withvarying DIPA-15EO concentrations (aq.) at 25° C. (Oil A (85% w/v) NaCl(0.2% aq.)).

FIG. 3: Apparent viscosity of oil 85% A emulsions vs. shear rate atdifferent temperature (ARES Rheometer measurements) (Oil A (85% w/v)NaCl (0.4% aq.) DIPA-15EO (1.5% aq.)).

FIG. 4: Apparent viscosity of 85% oil A emulsions with varying emulsionstorage time at 25° C. (Oil A (85% w/v) NaCl (0.5% aq.) DIPA-15EO (2.5%aq.)).

FIG. 5: Apparent viscosity of oil A emulsions with 1.5% DIPA-15EO withvarying oil content at 25° C. (Oil A: DIPA-15EO (1.5% aq.) NaCl (0.2%aq.)).

FIG. 6: Apparent viscosity of oil A emulsions with 1.5% DIPA-15EO withvarying oil content at 25° C. (Oil A: DIPA-15EO (1.5% aq.) NaCl (1%aq.)).

FIG. 7: Apparent viscosity of 40% oil A emulsions with various amineco-solvents at 25° C. (Oil A (40% w/v) NaCl (0.1% aq.)).

FIG. 8: Apparent viscosity of 60% oil A emulsions with various amineco-solvents at 25° C. (Oil A (60% w/v) NaCl (0.1% aq.)).

FIG. 9: Apparent viscosity of oil A emulsions with combination of amineand phenol ethoxylate co-solvents at 25° C. (Oil A (% w/v) DIPA-15EO(1.5% aq.) Ph-10EO (0.5% aq.) NaCl (1% aq.)).

FIG. 10: Apparent viscosity of oil A emulsions with combination of amineco-solvent and T-Soft surfactant (Dodecylbenzene Sulfonic Acid (DDBSA))at 25° C. (Oil A (% w/v) DIPA-15EO (1.5% aq.) DDBSA (0.5% aq.) NaCl(0.2% aq.)).

FIG. 11: Apparent viscosity of oil C emulsions with combination ofethylene glycol and water at 25° C. (Oil C (80% w/v) DIPA-15EO (0.6%w/v) Ethylene Glycol (15% w/v) DI-H2O (4.4% w/v)).

FIG. 12. Viscosity versus shear rate with amines in heavy crude oil.

DETAILED DESCRIPTION OF THE INVENTION I. Definitions

The abbreviations used herein have their conventional meaning within thechemical and biological arts.

Where substituent groups are specified by their conventional chemicalformulae, written from left to right, they equally encompass thechemically identical substituents that would result from writing thestructure from right to left, e.g., —CH₂O— is equivalent to —OCH₂—.

The term “alkyl,” by itself or as part of another substituent, means,unless otherwise stated, a straight (i.e. unbranched) or branched chainwhich may be fully saturated, mono- or polyunsaturated and can includedi- and multivalent radicals, having the number of carbon atomsdesignated (i.e. C₁-C₁₀ means one to ten carbons). Examples of saturatedhydrocarbon radicals include, but are not limited to, groups such asmethyl, ethyl, n-propyl, isopropyl, n-butyl, t-butyl, isobutyl,sec-butyl, homologs and isomers of, for example, n-pentyl, n-hexyl,n-heptyl, n-octyl, and the like. An unsaturated alkyl group is onehaving one or more double bonds or triple bonds. Examples of unsaturatedalkyl groups include, but are not limited to, vinyl, 2-propenyl, crotyl,2-isopentenyl, 2-(butadienyl), 2,4-pentadienyl, 3-(1,4-pentadienyl),ethynyl, 1- and 3-propynyl, 3-butynyl, and the higher homologs andisomers. Alkyl groups which are limited to hydrocarbon groups are termed“homoalkyl”. An alkoxy is an alkyl attached to the remainder of themolecule via an oxygen linker (—O—).

The term “alkylene” by itself or as part of another substituent means adivalent radical derived from an alkyl, as exemplified, but not limited,by —CH₂CH₂CH₂CH₂—, and further includes those groups described below as“heteroalkylene.” Typically, an alkyl (or alkylene) group will have from1 to 24 carbon atoms, with those groups having 10 or fewer carbon atomsbeing preferred in the present invention. A “lower alkyl” or “loweralkylene” is a shorter chain alkyl or alkylene group, generally havingeight or fewer carbon atoms.

The term “heteroalkyl,” by itself or in combination with another term,means, unless otherwise stated, a stable straight or branched chain orcombinations thereof, consisting of at least one carbon atom and atleast one heteroatom selected from the group consisting of O, N, P, Siand S, and wherein the nitrogen and sulfur atoms may optionally beoxidized and the nitrogen heteroatom may optionally be quaternized. Theheteroatom(s) O, N, P and S and Si may be placed at any interiorposition of the heteroalkyl group or at the position at which the alkylgroup is attached to the remainder of the molecule. Examples include,but are not limited to, —CH₂—CH₂—O—CH₃, —CH₂—CH₂—NH—CH₃,—CH₂—CH₂—N(CH₃)—CH₃, —CH₂—S—CH₂—CH₃, —CH₂—CH₂, —S(O)—CH₃,—CH₂—CH₂—S(O)₂—CH₃, —CH═CH—O—CH₃, —Si(CH₃)₃, —CH₂—CH═N—OCH₃,—CH═CH—N(CH₃)—CH₃, —O—CH₃, —O—CH₂, —CH₃, and —CN. Up to two heteroatomsmay be consecutive, such as, for example, —CH₂—NH—OCH₃. Similarly, theterm “heteroalkylene” by itself or as part of another substituent meansa divalent radical derived from heteroalkyl, as exemplified, but notlimited by, —CH₂—CH₂—S—CH₂—CH₂— and —CH₂—S—CH₂—CH₂—NH—CH₂—. Forheteroalkylene groups, heteroatoms can also occupy either or both of thechain termini (e.g., alkyleneoxy, alkylenedioxy, alkyleneamino,alkylenediamino, and the like). Still further, for alkylene andheteroalkylene linking groups, no orientation of the linking group isimplied by the direction in which the formula of the linking group iswritten. For example, the formula —C(O)₂R′— represents both —C(O)₂R′—and —R′C(O)₂—.

The terms “cycloalkyl” and “heterocycloalkyl,” by themselves or incombination with other terms, represent, unless otherwise stated, cyclicversions of “alkyl” and “heteroalkyl”, respectively. Additionally, forheterocycloalkyl, a heteroatom can occupy the position at which theheterocycle is attached to the remainder of the molecule. Examples ofcycloalkyl include, but are not limited to, cyclopropyl, cyclobutyl,cyclopentyl, cyclohexyl, 1-cyclohexenyl, 3-cyclohexenyl, cycloheptyl,and the like. Examples of heterocycloalkyl include, but are not limitedto, 1-(1,2,5,6-tetrahydropyridyl), 1-piperidinyl, 2-piperidinyl,3-piperidinyl, 4-morpholinyl, 3-morpholinyl, tetrahydrofuran-2-yl,tetrahydrofuran-3-yl, tetrahydrothien-2-yl, tetrahydrothien-3-yl,1-piperazinyl, 2-piperazinyl, and the like. A “cycloalkylene” and a“heterocycloalkylene,” alone or as part of another substituent means adivalent radical derived from a cycloalkyl and heterocycloalkyl,respectively.

The term “aryl” means, unless otherwise stated, a polyunsaturated,aromatic, hydrocarbon substituent which can be a single ring or multiplerings (preferably from 1 to 3 rings) which are fused together (i.e. afused ring aryl) or linked covalently. A fused ring aryl refers tomultiple rings fused together wherein at least one of the fused rings isan aryl ring. The term “heteroaryl” refers to aryl groups (or rings)that contain from one to four heteroatoms selected from N, O, and S,wherein the nitrogen and sulfur atoms are optionally oxidized, and thenitrogen atom(s) are optionally quaternized. Thus, the term “heteroaryl”includes fused ring heteroaryl groups (i.e. multiple rings fusedtogether wherein at least one of the fused rings is a heteroaromaticring). A 5,6-fused ring heteroarylene refers to two rings fusedtogether, wherein one ring has 5 members and the other ring has 6members, and wherein at least one ring is a heteroaryl ring. Likewise, a6,6-fused ring heteroarylene refers to two rings fused together, whereinone ring has 6 members and the other ring has 6 members, and wherein atleast one ring is a heteroaryl ring. And a 6,5-fused ring heteroarylenerefers to two rings fused together, wherein one ring has 6 members andthe other ring has 5 members, and wherein at least one ring is aheteroaryl ring. A heteroaryl group can be attached to the remainder ofthe molecule through a carbon or heteroatom. Non-limiting examples ofaryl and heteroaryl groups include phenyl, 1-naphthyl, 2-naphthyl,4-biphenyl, 1-pyrrolyl, 2-pyrrolyl, 3-pyrrolyl, 3-pyrazolyl,2-imidazolyl, 4-imidazolyl, pyrazinyl, 2-oxazolyl, 4-oxazolyl,2-phenyl-4-oxazolyl, 5-oxazolyl, 3-isoxazolyl, 4-isoxazolyl,5-isoxazolyl, 2-thiazolyl, 4-thiazolyl, 5-thiazolyl, 2-furyl, 3-furyl,2-thienyl, 3-thienyl, 2-pyridyl, 3-pyridyl, 4-pyridyl, 2-pyrimidyl,4-pyrimidyl, 5-benzothiazolyl, purinyl, 2-benzimidazolyl, 5-indolyl,1-isoquinolyl, 5-isoquinolyl, 2-quinoxalinyl, 5-quinoxalinyl,3-quinolyl, and 6-quinolyl. Substituents for each of the above notedaryl and heteroaryl ring systems are selected from the group ofacceptable substituents described below. An “arylene” and a“heteroarylene,” alone or as part of another substituent means adivalent radical derived from an aryl and heteroaryl, respectively.

Where a substituent of a compound provided herein is “R-substituted”(e.g. R⁷-substituted), it is meant that the substituent is substitutedwith one or more of the named R groups (e.g. R⁷) as appropriate. In someembodiments, the substituent is substituted with only one of the named Rgroups.

The symbol “

” denotes the point of attachment of a chemical moiety to the remainderof a molecule or chemical formula.

Each R-group as provided in the formulae provided herein can appear morethan once. Where an R-group appears more than once each R group can beoptionally different.

The term “contacting” as used herein, refers to materials or compoundsbeing sufficiently close in proximity to react or interact. For example,in methods of contacting a hydrocarbon material bearing formation and/ora wellbore, the term “contacting” includes placing an aqueouscomposition (including for example chemical, co-solvent or polymer)within a hydrocarbon material bearing formation using any suitablemanner known in the art (e.g., pumping, injecting, pouring, releasing,displacing, spotting or circulating the chemical into a well, wellboreor hydrocarbon bearing formation).

The terms “unrefined petroleum” and “crude oil” are used interchangeablyand in keeping with the plain ordinary usage of those terms. “Unrefinedpetroleum” and “crude oil” may be found in a variety of petroleumreservoirs (also referred to herein as a “reservoir,” “oil fielddeposit” “deposit” and the like) and in a variety of forms includingoleaginous materials, oil shales (i.e. organic-rich fine-grainedsedimentary rock), tar sands, light oil deposits, heavy oil deposits,and the like. “Crude oils” or “unrefined petroleums” generally refer toa mixture of naturally occurring hydrocarbons that may be refined intodiesel, gasoline, heating oil, jet fuel, kerosene, and other productscalled fuels or petrochemicals. Crude oils or unrefined petroleums arenamed according to their contents and origins, and are classifiedaccording to their per unit weight (specific gravity). Heavier crudesgenerally yield more heat upon burning, but have lower gravity asdefined by the American Petroleum Institute (API) and market price incomparison to light (or sweet) crude oils. Crude oil may also becharacterized by its Equivalent Alkane Carbon Number (EACN).

Crude oils vary widely in appearance and viscosity from field to field.They range in color, odor, and in the properties they contain. While allcrude oils are mostly hydrocarbons, the differences in properties,especially the variation in molecular structure, determine whether acrude oil is more or less easy to produce, pipeline, and refine. Thevariations may even influence its suitability for certain products andthe quality of those products. Crude oils are roughly classified intothree groups, according to the nature of the hydrocarbons they contain.(i) Paraffin based crude oils contain higher molecular weight paraffins,which are solid at room temperature, but little or no asphaltic(bituminous) matter. They can produce high-grade lubricating oils. (ii)Asphaltene based crude oils contain large proportions of asphalticmatter, and little or no paraffin. Some are predominantly naphthenes andso yield lubricating oils that are sensitive to temperature changes thanthe paraffin-based crudes. (iii) Mixed based crude oils contain bothparaffin and naphthenes, as well as aromatic hydrocarbons. Most crudeoils fit this latter category.

“Heavy crude oils” as provided herein are crude oils, with an APIgravity of less than 20, or a viscosity of at least 100 cp. The heavycrude oils may have a viscosity greater than 100 cP. In someembodiments, the heavy crude oil has a viscosity of at least 100 cP. Inother embodiments, the heavy crude oil has a viscosity of at least 1,000cP. In other embodiments, the heavy crude oil has a viscosity of atleast 10,000 cP. In other embodiments, the heavy crude oil has aviscosity of at least 100,000 cP. In other embodiments, the heavy crudeoil has a viscosity of at least 1,000,000 cP.

“Reactive” or “active” heavy crude oil as referred to herein is crudeoil containing natural organic acidic components (also referred toherein as unrefined petroleum acid) or their precursors such as estersor lactones. These active heavy crude oils can generate soaps(carboxylate surfactants) when reacted with alkali or other basic agents(e.g. a basic co-solvent as provided herein). More terms usedinterchangeably for heavy crude oil throughout this disclosure areactive hydrocarbon material or active petroleum material. An “oil bank”or “oil cut” as referred to herein, is the heavy crude oil that does notcontain the injected chemicals and is pushed by the injected fluidduring an enhanced oil recovery process. A “nonactive oil,” as usedherein, refers to an oil that is not substantially reactive or crude oilnot containing significant amounts of natural organic acidic componentsor their precursors such as esters or lactones such that significantamounts of soaps are generated when reacted with alkali or other basicagents (e.g. a basic co-solvent as provided herein). A nonactive oil asreferred to herein includes oils having an acid number of less than 0.5mg KOH/g of oil.

“Unrefined petroleum acids” as referred to herein are carboxylic acidscontained in active petroleum material (reactive heavy crude oil). Theunrefined petroleum acids contain C₁₁ to C₂₀ alkyl chains, includingnapthenic acid mixtures. The recovery of such “reactive” oils may beperformed using alkali (e.g. NaOH or Na₂CO₃) or other basic agents (e.g.a basic co-solvent as provided herein) in a composition. The alkali orother basic agent (e.g. a basic co-solvent as provided herein) reactswith the acid in the reactive oil to form soap in situ. These in situgenerated soaps serve as a source of surfactants enabling efficient oilrecovery from the reservoir.

The term “polymer” refers to a molecule having a structure thatessentially includes the multiple repetitions of units derived, actuallyor conceptually, from molecules of low relative molecular mass. In someembodiments, the polymer is an oligomer.

The term “bonded” refers to having at least one of covalent bonding,hydrogen bonding, ionic bonding, Van Der Waals interactions, piinteractions, London forces or electrostatic interactions.

The term “productivity” as applied to a petroleum or oil well refers tothe capacity of a well to produce hydrocarbons (e.g. unrefinedpetroleum); that is, the ratio of the hydrocarbon flow rate to thepressure drop, where the pressure drop is the difference between theaverage reservoir pressure and the flowing bottom hole well pressure(i.e., flow per unit of driving force).

The term “oil solubilization ratio” is defined as the volume of oilsolubilized divided by the volume of surfactant in microemulsion. Allthe surfactant is presumed to be in the microemulsion phase. The oilsolubilization ratio is applied for Winsor type I and type III behavior.The volume of oil solubilized is found by reading the change betweeninitial aqueous level and excess oil (top) interface level. The oilsolubilization ratio is calculated as follows:

${\sigma_{o} = \frac{V_{o}}{V_{s}}},$

whereinσ_(o)=oil solubilization ratio;V_(o)=volume of oil solubilized;V_(s)=volume of surfactant.

The term “water solubilization ratio” is defined as the volume of watersolubilized divided by the volume of surfactant in microemulsion. Allthe surfactant is presumed to be in the microemulsion phase. The watersolubilization ratio is applied for Winsor type III and type IIbehavior. The volume of water solubilized is found by reading the changebetween initial aqueous level and excess water (bottom) interface level.The water solubilization parameter is calculated as follows:

${\sigma_{w} = \frac{V_{w}}{V_{s}}},$

whereinσ_(w)=water solubilization ratio;V_(w)=volume of water solubilized.

The optimum solubilization ratio occurs where the oil and watersolubilization ratios are equal. The coarse nature of phase behaviorscreening often does not include a data point at optimum, so thesolubilization ratio curves are drawn for the oil and watersolubilization ratio data and the intersection of these two curves isdefined as the optimum. The following is true for the optimumsolubilization ratio:

σ_(O)=σ_(w)=σ*;

σ*=optimum solubilization ratio.

The term “solubility” or “solubilization” in general refers to theproperty of a solute, which can be a solid, liquid or gas, to dissolvein a solid, liquid or gaseous solvent thereby forming a homogenoussolution of the solute in the solvent. Solubility occurs under dynamicequilibrium, which means that solubility results from the simultaneousand opposing processes of dissolution and phase joining (e.g.precipitation of solids). The solubility equilibrium occurs when the twoprocesses proceed at a constant rate. The solubility of a given solutein a given solvent typically depends on temperature. For many solidsdissolved in liquid water, the solubility increases with temperature. Inliquid water at high temperatures, the solubility of ionic solutes tendsto decrease due to the change of properties and structure of liquidwater. In more particular, solubility and solubilization as referred toherein are the properties of oil to dissolve in water and vice versa.

“Viscosity” refers to a fluid's internal resistance to flow or beingdeformed by shear or tensile stress. In other words, viscosity may bedefined as thickness or internal friction of a liquid. Thus, water is“thin”, having a lower viscosity, while oil is “thick”, having a higherviscosity. More generally, the less viscous a fluid is, the greater itsease of fluidity.

The term “salinity” as used herein, refers to concentration of saltdissolved in a aqueous phases. Examples for such salts are withoutlimitation, sodium chloride, magnesium and calcium sulfates, andbicarbonates. In more particular, the term salinity as it pertains tothe present invention refers to the concentration of salts in brine andsurfactant solutions.

The term “aqueous solution or aqueous formulation” refers to a solutionin which the solvent is water. The term “emulsion, emulsion solution oremulsion formulation” refers to a mixture of two or more liquids whichare normally immiscible. A non-limiting example for an emulsion is amixture of oil and water.

An “alkali agent” is used according to its conventional meaning andincludes basic, ionic salts of alkali metals or alkaline earth metals.Alkali agents as provided herein are typically capable of reacting withan unrefined petroleum acid (e.g. the acid or its precursor in crude oil(reactive oil)) to form soap (a surfactant which is a salt of a fattyacid) in situ. These in situ generated soaps serve as a source ofsurfactants causing a reduction of the interfacial tension of the oil inwater emulsion, thereby reducing the viscosity of the emulsion. Examplesof alkali agents useful for the provided invention include, but are notlimited to, sodium hydroxide, sodium carbonate, sodium silicate, sodiummetaborate, and EDTA tetrasodium salt.

A “co-solvent” refers to a compound having the ability to increase thesolubility of a solute (e.g., a polymer, an alkali agent) in thepresence of an unrefined petroleum acid. In some embodiments, thecompounds provided herein (e.g., an alkylamine or a compound of formula(I), (II), or (III)) including embodiments thereof are basicco-solvents. A “basic co-solvent” refers to a compound capable ofaccepting protons (e.g. compounds including a basic nitrogen atom) andreacting with an unrefined petroleum acid (e.g. the acid in crude oil(reactive oil)) to form soap (a surfactant salt of a fatty acid), forexample, in situ.

The term “alkylamine” is used according to its ordinary meaning andrefers to a heteroalkyl compound composed of one or more nitrogenheteroatoms, carbon atoms (e.g. C₁-C₆ alkyl or alkylene groups) andhydrogen atoms wherein at least one nitrogen atom is basic. In someembodiments, the alkylamine is a secondary amine (e.g.,diisopropylamine). A “secondary amine” as provided herein is usedaccording to its ordinary meaning and refers to an organic compoundwherein the nitrogen atom is bound to a hydrogen atom and twonon-hydrogen substituents, wherein the two non-hydrogen substituents areindependently aryl or alkyl. In other embodiments, the alkylamine is analkylpolyamine. An “alkylpolyamine” as provided herein is used accordingto its ordinary meaning and refers to an alkylamine having a pluralityof nitrogen heteroatoms (e.g. NH₂ or NH group). Non limiting examples ofalkylpolyamines are dimethylaminopropylamine (DMAPA),triethylenetetramine (TETA), and diethylenetriamine (DETA). Thealkylamine or alkylpolyamine as provided herein may include saturatedC₁-C₆ alkyl or alkylene bound to another substituent (e.g., R^(1A) orR^(1B)).

The term “arylamine” is used according to its ordinary meaning andrefers to a saturated 5 to 10 membered aryl ring substituted with atleast one NH₂ group. A non-limiting example of an arylamine useful forthe compositions provided herein is aniline.

An “alkylamine alkoxylate” as provided herein is used according to itsordinary meaning and refers to an alkylamine in which a nitrogenheteroatom is bonded to a hydrophilic moiety including an alcohol and/oran alkoxy portion. The term “alcohol” is used according to its ordinarymeaning and refers to an organic compound containing an —OH groupattached to a carbon atom. The term “alkoxy” refers to an alkyl (e.g.C₁-C₄ alkyl) group singularly bonded to oxygen. The alkoxy may be anethoxy (—CH₂—CH₂—O—), a propoxy (—CH₂—CH(methyl)-O—) or a butoxy(—CH₂—CH(ethyl)-O—) group.

A “microemulsion” as referred to herein is a thermodynamically stablemixture of oil and water that may also include additional componentssuch as the co-solvents provided herein including embodiments thereof,electrolytes, alkali and polymers. In contrast, a “macroemulsion” asreferred to herein is a thermodynamically unstable mixture of oil andwater that may also include additional components. The emulsioncomposition provided herein may be an oil-in-water emulsion, wherein thein situ generated soap aggregates (e.g. micelles) include a hydrophilicportion contacting the aqueous phase of the emulsion and a lipophilicportion contacting the oil phase of the emulsion. Thus, in someembodiments, the in situ generated soap forms part of the aqueous phaseof the emulsion. And in other embodiments, the in situ generated soapforms part of the oil phase of the emulsion. In yet another embodiment,the in situ generated soap forms part of an interface between theaqueous phase and the oil phase of the emulsion.

A “catalyst” as referred to herein is an agent used to convert unrefinedpetroleum, typically heaving low octane ratings, into high-octane liquidreformates, which are components of high-octane gasoline. During theprocess of conversion, the hydrocarbon molecules in the unrefinedpetroleum may be restructured and broken up into smaller molecules. Thereformate produced by the conversion process may contain hydrocarbonswith more complex molecular shapes having higher octane values than thehydrocarbons in the unrefined petroleum. Examples of catalysts usefulfor the conversion of unrefined petroleum into lighter high-octanereformates are without limitation, nanoparticles, platinum, palladium,rhodium, nickel, chromium oxide, Pt/Al₂O₃, zinc titanium oxide, aluminumoxide, and zeolites.

A “production well” as referred to herein is a vessel used for enhancedoil recovery, which connects a petroleum reservoir to the surface. Aproduction well is capable of transporting crude oil that has beenextracted from the petroleum reservoir (extracted crude oil) to thesurface. In embodiments, the production well is in close proximity tothe petroleum reservoir. In embodiments, the production well isconnected to the reservoir through a mechanical pump (e.g., electricalsubmersible pump). In embodiments, the production well includes amechanical pump.

An “extracted heavy crude oil” as referred to herein is a heavy crudeoil that has exited a petroleum reservoir. An extracted heavy crude oildoes not form part of the reservoir in which it was endogenouslypresent. In embodiments, the extracted heavy crude oil is within aproduction well. In embodiments, the extracted heavy crude oil is withina transportation vessel. In embodiments, the extracted heavy crude oilis within a transport vessel. In embodiments, the extracted heavy crudeoil is within a pipeline.

II. Compositions

While the making and using of various embodiments of the presentinvention are discussed in detail below, it should be appreciated thatthe present invention provides many applicable inventive concepts thatcan be embodied in a wide variety of specific contexts. The specificembodiments discussed herein are merely illustrative of specific ways tomake and use the invention and do not limit the scope of the invention.

Provided herein are, inter alia, heavy crude oil emulsion compositionsto be used for a variety of applications including transport of heavycrude oils. The heavy crude oil emulsions provided herein may be usedwith a wide variety of heavy crude oil concentrations and at a widerange of salinity, including hard brine and soft brine. In embodiments,the viscosity of the heavy crude oil emulsion compositions providedherein is surprisingly much lower than the viscosity of the heavy crudeoil. Further, the viscosity of the heavy crude oil emulsions providedherein may remain low at ambient temperatures (i.e. temperatures below80° C.) over extended periods of time, making them particularly usefulfor heavy crude oil transport.

In one aspect, a heavy crude oil emulsion is provided. The heavy crudeoil emulsion includes a heavy crude oil, water and a co-solvent. Theco-solvent is an alkylamine or a compound having the formula:

In formula (I) R^(1A) and R^(1B) are independently hydrogen,unsubstituted C₁-C₈ alkyl, unsubstituted cycloalkyl, unsubstitutedheterocycloalkyl, unsubstituted aryl, unsubstituted heteroaryl, C₁-C₆alkylamine or

R² and R³ are independently hydrogen or unsubstituted C₁-C₂ alkyl. Thesymbol n is an integer from 1 to 30. The symbol m is an integer from 1to 30 and the heavy crude oil emulsion is within a transport vessel.

The heavy crude oil emulsion provided herein including embodimentsthereof includes a heavy crude oil, water and a co-solvent and theco-solvent may be a compound of formula (I). In formula (I) n may be inan integer from 1 to 30. Thus, in some embodiments, the symbol n is aninteger from 1-30. In some embodiments, the symbol n is an integer from1-28. In other embodiments, the symbol n is an integer from 1-26. Insome embodiments, the symbol n is an integer from 1-24. In someembodiments, the symbol n is an integer from 1-22. In some embodiments,the symbol n is an integer from 1-20. In some embodiments, the symbol nis an integer from 1-18. In some embodiments, the symbol n is an integerfrom 1-16. In some embodiments, the symbol n is an integer from 1-14. Insome embodiments, the symbol n is an integer from 1-12. In someembodiments, the symbol n is an integer from 1-10. In some embodiments,the symbol n is an integer from 1-8. In some embodiments, the symbol nis an integer from 1-6. In some embodiments, the symbol n is an integerfrom 1-4. In some embodiments, the symbol n is an integer from 1-3. Insome embodiment, the symbol n is 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12,13, 14, 15, 16, 17, 18, 19, 20, 21, 22, 23, 24, 25, 26, 27, 28, 29, or30. In one embodiment, the symbol n is 3. In other embodiments, thesymbol n is 1. In one embodiment, the symbol n is 6.

In some related embodiments, R² is hydrogen and n is as defined in anembodiment above (e.g., n is at least 1, or at least 10). Thus, in someembodiments, R² is hydrogen and n is 1. In other embodiments, R² ishydrogen and n is 3.

In some embodiments, the symbol m is an integer from 1-30. In someembodiments, the symbol m is an integer from 1-28. In other embodiments,the symbol m is an integer from 1-26. In some embodiments, the symbol mis an integer from 1-24. In some embodiments, the symbol m is an integerfrom 1-22. In some embodiments, the symbol m is an integer from 1-20. Insome embodiments, the symbol m is an integer from 1-18. In someembodiments, the symbol m is an integer from 1-16. In some embodiments,the symbol m is an integer from 1-14. In some embodiments, the symbol mis an integer from 1-12. In some embodiments, the symbol m is an integerfrom 1-10. In some embodiments, the symbol m is an integer from 1-8. Insome embodiments, the symbol m is an integer from 1-6. In someembodiments, the symbol m is an integer from 1-4. In some embodiments,the symbol m is an integer from 1-3. In some embodiment, the symbol m is1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20,21, 22, 23, 24, 25, 26, 27, 28, 29, or 30. In one embodiment, the symbolm is 3. In other embodiments, the symbol m is 1. In one embodiment, thesymbol m is 6.

In some related embodiments, R³ is hydrogen and m is as defined in anembodiment above (e.g., n is at least 1, or at least 10). Thus, in someembodiments, R³ is hydrogen and m is 1. In other embodiments, R³ ishydrogen and m is 3.

As provided herein R^(1A) and R^(1B) may be independently hydrogen,unsubstituted C₁-C₈ (e.g., C₁-C₄) alkyl, unsubstituted C₃-C₆ (e.g., C₆)cycloalkyl, unsubstituted 3 to 8 membered (e.g., 6 membered)heterocycloalkyl, C₅-C₈ (e.g., C₆) unsubstituted aryl, unsubstituted 5to 8 membered (e.g., 5 to 6-membered) heteroaryl, C₁-C₆ (e.g. C₂-C₄)alkylamine or

In some embodiments, R^(1A) and R^(1B) are independently unsubstitutedC₁-C₈ alkyl. In other embodiments, R^(1A) and R^(1B) are independentlyunsubstituted C₁-C₆ alkyl. In other embodiments, R^(1A) and R^(1B) areindependently unsubstituted C₁-C₄ alkyl. In some embodiments, R^(1A) andR^(1B) are unsubstituted C₃ alkyl. In some embodiments, the number oftotal carbon atoms within R^(1A) and R^(1B) combined does not exceed 8.

In some embodiments, R^(1A) and R^(1B) are independently branched orlinear unsubstituted C₁-C₈ alkyl. In other embodiments, R^(1A) andR^(1B) are independently branched or linear unsubstituted C₁-C₆ alkyl.In other embodiments, R^(1A) and R^(1B) are independently branched orlinear unsubstituted C₁-C₄ alkyl. In some embodiments, R^(1A) and R^(1B)are independently branched or linear unsubstituted C₃ alkyl. In someembodiments, R^(1A) and R^(1B) are independently linear unsubstitutedC₁-C₈ alkyl. In other embodiments, R^(1A) and R^(1B) are independentlybranched unsubstituted C₁-C₈ alkyl. In some embodiments, R^(1A) andR^(1B) are independently linear unsubstituted C₁-C₆ alkyl. In otherembodiments, R^(1A) and R^(1B) are independently branched unsubstitutedC₁-C₆ alkyl. In some embodiments, R^(1A) and R^(1B) are independentlylinear unsubstituted C₁-C₄ alkyl. In other embodiments, R^(1A) andR^(1B) are independently branched unsubstituted C₁-C₄ alkyl. In someembodiments, R^(1A) and R^(1B) are linear unsubstituted C₃ alkyl. Inother embodiments, R^(1A) and R^(1B) are branched unsubstituted C₃alkyl. In some embodiments, R^(1A) and R^(1B) are unsubstitutedisopropyl.

As provided herein R^(1A) and R^(1B) may be independently hydrogen orC₁-C₆ (e.g., C₁-C₄) alkylamine. In some embodiments, R^(1A) and R^(1B)are independently hydrogen or C₁-C₆ alkylamine. In other embodiments,R^(1A) and R^(1B) are independently hydrogen or C₂-C₆ alkylamine. Insome embodiments, R^(1A) and R^(1B) are independently hydrogen or C₃-C₆alkylamine. In other embodiments, R^(1A) and R^(1B) are independentlyhydrogen or C₄-C₆ alkylamine. In some embodiments, R^(1A) and R^(1B) areindependently hydrogen or C₄ alkylamine. In other embodiments, R^(1A)and R^(1B) are independently hydrogen or C₅ alkylamine. In someembodiments, R^(1A) and R^(1B) are independently hydrogen or C₆alkylamine.

In some embodiments, R^(1A) and R^(1B) are independently hydrogen orbranched or linear C₁-C₆ alkylamine. In other embodiments, R^(1A) andR^(1B) are independently hydrogen or branched or linear C₂-C₆alkylamine. In some embodiments, R^(1A) and R^(1B) are independentlyhydrogen or branched or linear C₃-C₆ alkylamine. In other embodiments,R^(1A) and R^(1B) are independently hydrogen or branched or linear C₄-C₆alkylamine. In some embodiments, R^(1A) and R^(1B) are independentlyhydrogen or branched or linear C₄ alkylamine. In other embodiments,R^(1A) and R^(1B) are independently hydrogen or branched or linear C₅alkylamine. In some embodiments, R^(1A) and R^(1B) are independentlyhydrogen or branched or linear C₆ alkylamine.

In some embodiments, R^(1A) and R^(1B) are independently hydrogen orlinear C₁-C₆ alkylamine. In other embodiments, R^(1A) and R^(1B) areindependently hydrogen or linear C₂-C₆ alkylamine. In some embodiments,R^(1A) and R^(1B) are independently hydrogen or linear C₃-C₆ alkylamine.In other embodiments, R^(1A) and R^(1B) are independently hydrogen orlinear C₄-C₆ alkylamine. In some embodiments, R^(1A) and R^(1B) areindependently hydrogen or linear C₄ alkylamine. In other embodiments,R^(1A) and R^(1B) are independently hydrogen or linear C₅ alkylamine. Insome embodiments, R^(1A) and R^(1B) are independently hydrogen or linearC₆ alkylamine. In some embodiments, R^(1A) and R^(1B) are independentlyhydrogen or branched C₁-C₆ alkylamine. In other embodiments, R^(1A) andR^(1B) are independently hydrogen or branched C₂-C₆ alkylamine. In someembodiments, R^(1A) and R^(1B) are independently hydrogen or branchedC₃-C₆ alkylamine. In other embodiments, R^(1A) and R^(1B) areindependently hydrogen or branched C₄-C₆ alkylamine. In someembodiments, R^(1A) and R^(1B) are independently hydrogen or branched C₄alkylamine. In other embodiments, R^(1A) and R^(1B) are independentlyhydrogen or branched C₅ alkylamine. In some embodiments, R^(1A) andR^(1B) are independently hydrogen or branched C₆ alkylamine.

In some embodiments, R^(1A) is hydrogen and R^(1B) is C₄-C₆ alkylamine.In other embodiments, R^(1A) is hydrogen and R^(1B) is branched orlinear C₄-C₆ alkylamine. In some embodiments, R^(1A) is hydrogen andR^(1B) is linear C₄-C₆ alkylamine. In other embodiments, R^(1A) ishydrogen and R^(1B) is branched C₄-C₆ alkylamine. In some embodiments,R^(1A) is hydrogen and R^(1B) is C₄ alkylamine. In some embodiments,R^(1A) is hydrogen and R^(1B) is linear C₄ alkylamine. In otherembodiments, R^(1A) is hydrogen and R^(1B) is C₅ alkylamine. In otherembodiments, R^(1A) is hydrogen and R^(1B) is linear C₅ alkylamine. Inother embodiments, R^(1A) is hydrogen and R^(1B) is C₆ alkylamine. Inother embodiments, R^(1A) is hydrogen and R^(1B) is linear C₆alkylamine.

R^(1A) and R^(1B) may be independently C₁-C₆ (e.g., C₁-C₄) alkylamine.In some embodiments, R^(1A) and R^(1B) are independently C₁-C₆alkylamine. In other embodiments, R^(1A) and R^(1B) are independentlyC₂-C₆ alkylamine. In other embodiments, R^(1A) and R^(1B) areindependently C₃-C₆ alkylamine. In other embodiments, R^(1A) and R^(1B)are independently C₄-C₆ alkylamine. In some embodiments, R^(1A) andR^(1B) are independently branched or linear C₁-C₆ alkylamine. In otherembodiments, R^(1A) and R^(1B) are independently branched or linearC₂-C₆ alkylamine. In other embodiments, R^(1A) and R^(1B) areindependently branched or linear C₃-C₆ alkylamine. In other embodiments,R^(1A) and R^(1B) are independently branched or linear C₄-C₆ alkylamine.In some embodiments, R^(1A) and R^(1B) are independently linear C₁-C₆alkylamine. In other embodiments, R^(1A) and R^(1B) are independentlylinear C₂-C₆ alkylamine. In other embodiments, R^(1A) and R^(1B) areindependently linear C₃-C₆ alkylamine. In other embodiments, R^(1A) andR^(1B) are independently linear C₄-C₆ alkylamine. In some embodiments,R^(1A) and R^(1B) are independently branched C₁-C₆ alkylamine. In otherembodiments, R^(1A) and R^(1B) are independently branched C₂-C₆alkylamine. In other embodiments, R^(1A) and R^(1B) are independentlybranched C₃-C₆ alkylamine. In other embodiments, R^(1A) and R^(1B) areindependently branched C₄-C₆ alkylamine. In some embodiments, R^(1A) andR^(1B) are independently C₂ alkylamine or C₄ alkylamine. In someembodiments, R^(1A) and R^(1B) are C₂ alkylamine.

As described herein R^(1A) and R^(1B) may be an alkylpolyamine. Thus, insome embodiments, the alkylamine is an alkylpolyamine. In someembodiments, R^(1A) and R^(1B) are independently C₁-C₆ alkylpolyamine.In other embodiments, R^(1A) and R^(1B) are independently C₂-C₆alkylpolyamine. In other embodiments, R^(1A) and R^(1B) areindependently C₃-C₆ alkylpolyamine. In other embodiments, R^(1A) andR^(1B) are independently C₄-C₆ alkylpolyamine. In some embodiments,R^(1A) and R^(1B) are independently branched or linear C₁-C₆alkylpolyamine. In other embodiments, R^(1A) and R^(1B) areindependently branched or linear C₂-C₆ alkylpolyamine. In otherembodiments, R^(1A) and R^(1B) are independently branched or linearC₃-C₆ alkylpolyamine. In other embodiments, R^(1A) and R^(1B) areindependently branched or linear C₄-C₆ alkylpolyamine. In someembodiments, R^(1A) and R^(1B) are independently linear C₁-C₆alkylpolyamine. In other embodiments, R^(1A) and R^(1B) areindependently linear C₂-C₆ alkylpolyamine. In other embodiments, R^(1A)and R^(1B) are independently linear C₃-C₆ alkylpolyamine. In otherembodiments, R^(1A) and R^(1B) are independently linear C₄-C₆alkylpolyamine. In some embodiments, R^(1A) and R^(1B) are independentlybranched C₁-C₆ alkylpolyamine. In other embodiments, R^(1A) and R^(1B)are independently branched C₂-C₆ alkylpolyamine. In other embodiments,R^(1A) and R^(1B) are independently branched C₃-C₆ alkylpolyamine. Inother embodiments, R^(1A) and R^(1B) are independently branched C₄-C₆alkylpolyamine. In some embodiments, R^(1A) and R^(1B) are independentlyC₂ alkylamine or C₄ alkylpolyamine.

In some embodiments, R^(1A) and R^(1B) are independently hydrogen orC₁-C₆ alkylamine. In other embodiments, R^(1A) and R^(1B) are C₁-C₆alkylamine. In some embodiments, R^(1A) and R^(1B) are C₁-C₆alkylpolyamine. In the embodiments provided herein R^(1A) and R^(1B) mayhave the structure of formula:

In some embodiments, R^(1A) is hydrogen and R^(1B) has the structure offormula

In other embodiments, R^(1A) is hydrogen and R^(1B) has the structure offormula

In other embodiments, R^(1A) is hydrogen and R^(1B) has the structure offormula

In some embodiments, R^(1A) has the structure of formula

and R^(1B) has the structure of formula

In other embodiments, R^(1A) and R^(1B) have the structure of formula

As provided herein R^(1A) and R^(1B) may be independently hydrogen,unsubstituted C₃-C₆ (e.g., C₆) cycloalkyl or C₅-C₈ (e.g., C₆)unsubstituted aryl. Thus, in some embodiments, R^(1A) is hydrogen andR^(1B) is unsubstituted (e.g., C₃-C₆) cycloalkyl. In some embodiments,R^(1B) is unsubstituted 6 membered cycloalkyl. In other embodiments,R^(1A) is hydrogen and R^(1B) is (e.g., C₅-C₈) unsubstituted aryl. Insome embodiments, R^(1B) is phenyl.

As provided herein R² and R³ may be independently hydrogen orunsubstituted C₁-C₂ alkyl. Thus, in some embodiments, R² and R³ areindependently hydrogen, methyl or ethyl. In some embodiments, wheremultiple R² substituents are present and at least two R² substituentsare different, R² substituents with the fewest number of carbons arepresent to the side of the compound of formula (I), (II), or (III) boundto the hydrogen atom. In this embodiment, the compound of formula (I),(II), or (III) will be increasingly hydrophilic in progressing from thenitrogen to the side of the compound of formula (I), (II), or (III)bound to the hydrogen atom. The term “side of the compound of formula(I), (II), or (III) bound to the hydrogen atom” refers to the side ofthe compound indicated by asterisk in the below structures:

In some embodiments, the compound has the formula:

In formula (II) R^(1A) and R^(1B) are defined as above (e.g. hydrogen,C₃ alkyl, or C₁-C₆ alkylamine), R² is methyl or ethyl, o is an integerfrom 0 to 15 and p is an integer from 1 to 10. In some embodiments, R²is hydrogen, o is 0 and p is 1 to 6.

In some embodiments, o is 0 to 15. In some related embodiments, o is 0to 12. In some related embodiments, o is 0 to 10. In some relatedembodiments, o is 0 to 8. In some related embodiments, o is 0 to 6. Insome related embodiments, o is 0 to 4. In some related embodiments, o is0 to 2. In still further related embodiments, o is 0. In some furtherrelated embodiment, p is 1 to 10. In some further related embodiment, pis 1 to 8. In some further related embodiment, p is 1 to 6. In somefurther related embodiment, p is 1 to 4. In some further relatedembodiment, p is 1 to 2. In still some further related embodiment, p ismore than 1. In some further embodiment, p is 6. R^(1A), R^(1B) and R²may be any of the embodiments described above (e.g., R^(1A) and R^(1B)maybe isopropyl, R² maybe hydrogen or unsubstituted C₁-C₂ alkyl). Thus,in some embodiment, R^(1A) and R^(1B) are isopropyl, o is 0 and p is 3.

In some embodiments, o is 1 to 15. In some related embodiments, o is 1to 12. In some related embodiments, o is 1 to 10. In some relatedembodiments, o is 1 to 8. In some related embodiments, o is 1 to 6. Insome related embodiments, o is 1 to 4. In some related embodiments, o is1 to 2. In some further related embodiment, p is 1 to 10. In somefurther related embodiment, p is 1 to 8. In some further relatedembodiment, p is 1 to 6. In some further related embodiment, p is 1 to4. In some further related embodiment, p is 1 to 2. In still somefurther related embodiment, p is more than 1. R^(1A), R^(1B) and R² maybe any of the embodiments described above (e.g., R^(1A) and R^(1B) maybeisopropyl, R² maybe hydrogen or unsubstituted C₁-C₂ alkyl).

In some embodiments, o is 2 to 15. In some related embodiments, o is 2to 12. In some related embodiments, o is 2 to 10. In some relatedembodiments, o is 2 to 8. In some related embodiments, o is 2 to 6. Insome related embodiments, o is 2 to 4. In some further relatedembodiment, p is 1 to 10. In some further related embodiment, p is 1 to8. In some further related embodiment, p is 1 to 6. In some furtherrelated embodiment, p is 1 to 4. In some further related embodiment, pis 1 to 2. In still some further related embodiment, p is more than 1.R^(1A), R^(1B) and R² may be any of the embodiments described above(e.g., R^(1A) and R^(1B) maybe isopropyl, R² maybe hydrogen orunsubstituted C₁-C₂ alkyl).

In some embodiments, o is 4 to 15. In some related embodiments, o is 4to 12. In some related embodiments, o is 4 to 10. In some relatedembodiments, o is 4 to 8. In some related embodiments, o is 4 to 6. Insome further related embodiment, p is 1 to 10. In some further relatedembodiment, p is 1 to 8. In some further related embodiment, p is 1 to6. In some further related embodiment, p is 1 to 4. In some furtherrelated embodiment, p is 1 to 2. In still some further relatedembodiment, p is more than 1 R^(1A), R^(1B) and R² may be any of theembodiments described above (e.g., R^(1A) and R^(1B) maybe isopropyl, R²maybe hydrogen or unsubstituted C₁-C₂ alkyl).

In some embodiments, o is 6 to 15. In some related embodiments, o is 6to 12. In some related embodiments, o is 6 to 10. In some relatedembodiments, o is 6 to 8. In some further related embodiment, p is 1 to10. In some further related embodiment, p is 1 to 8. In some furtherrelated embodiment, p is 1 to 6. In some further related embodiment, pis 1 to 4. In some further related embodiment, p is 1 to 2. In stillsome further related embodiment, p is more than 1. R^(1A), R^(1B) and R²may be any of the embodiments described above (e.g., R^(1A) and R^(1B)maybe isopropyl, R² maybe hydrogen or unsubstituted C₁-C₂ alkyl).

In some embodiments, o is 8 to 15. In some related embodiments, o is 8to 12. In some related embodiments, o is 8 to 10. In some furtherrelated embodiment, p is 1 to 10. In some further related embodiment, pis 1 to 8. In some further related embodiment, p is 1 to 6. In somefurther related embodiment, p is 1 to 4. In some further relatedembodiment, p is 1 to 2. In still some further related embodiment, p ismore than 1. R^(1A), R^(1B) and R² may be any of the embodimentsdescribed above (e.g., R^(1A) and R^(1B) maybe isopropyl, R² maybehydrogen or unsubstituted C₁-C₂ alkyl).

In some embodiments, o is 10 to 15. In some related embodiments, o is 10to 12. In some further related embodiment, p is 1 to 10. In some furtherrelated embodiment, p is 1 to 8. In some further related embodiment, pis 1 to 6. In some further related embodiment, p is 1 to 4. In somefurther related embodiment, p is 1 to 2. In still some further relatedembodiment, p is more than 1. R^(1A), R^(1B) and R² may be any of theembodiments described above (e.g., R^(1A) and R^(1B) maybe isopropyl, R²maybe hydrogen or unsubstituted C₁-C₂ alkyl).

In some embodiments, o is 12 to 15. In some further related embodiment,p is 1 to 10. In some further related embodiment, p is 1 to 8. In somefurther related embodiment, p is 1 to 6. In some further relatedembodiment, p is 1 to 4. In some further related embodiment, p is 1 to2. In still some further related embodiment, p is more than 1. R^(1A),R^(1B) and R² may be any of the embodiments described above (e.g.,R^(1A) and R^(1B) maybe isopropyl, R² maybe hydrogen or unsubstitutedC₁-C₂ alkyl).

In other embodiments, the compound has the formula:

In formula (III) R² is ethyl, q is an integer from 0 to 10, r is aninteger from 0 to 10 and s is an integer from 1 to 10.

In some embodiment, q is 0 to 10. In some related embodiment, q is 1 to10. In some related embodiment, q is 2 to 10. In some relatedembodiment, q is 3 to 10. In some related embodiment, q is 4 to 10. Insome related embodiment, q is 5 to 10. In some related embodiment, q is6 to 10. In some related embodiment, q is 7 to 10. In some relatedembodiment, q is 8 to 10. In some related embodiment, q is 9 to 10.Moreover, in still further related embodiments, q is 0. In some furtherrelated embodiment, r is 0 to 10. In some further related embodiment, ris 1 to 10. In some further related embodiment, r is 2 to 10. In somefurther related embodiment, r is 3 to 10. In some further relatedembodiment, r is 4 to 10. In some further related embodiment, r is 5 to10. In some further related embodiment, r is 6 to 10. In some furtherrelated embodiment, r is 7 to 10. In some further related embodiment, ris 8 to 10. In some further related embodiment, r is 9 to 10. Moreover,in still further related embodiments, r is 0. In still some furtherembodiment, s is 1 to 10. In still some further embodiment, s is 2 to10. In still some further embodiment, s is 3 to 10. In still somefurther embodiment, s is 4 to 10. In still some further embodiment, s is5 to 10. In still some further embodiment, s is 6 to 10. In still somefurther embodiment, s is 7 to 10. In still some further embodiment, s is8 to 10. In still some further embodiment, s is 9 to 10. R^(1A), R^(1B)and R² may be any of the embodiments described above (e.g., R^(1A) andR^(1B) maybe isopropyl, R² maybe hydrogen or unsubstituted C₁-C₂ alkyl).

In some embodiment, q is 0 to 9. In some related embodiment, q is 1 to9. In some related embodiment, q is 2 to 9. In some related embodiment,q is 3 to 9. In some related embodiment, q is 4 to 9. In some relatedembodiment, q is 5 to 9. In some related embodiment, q is 6 to 9. Insome related embodiment, q is 7 to 9. In some related embodiment, q is 8to 9. Moreover, in still further related embodiments, q is 0. In somefurther related embodiment, r is 0 to 10. In some further relatedembodiment, r is 1 to 10. In some further related embodiment, r is 2 to10. In some further related embodiment, r is 3 to 10. In some furtherrelated embodiment, r is 4 to 10. In some further related embodiment, ris 5 to 10. In some further related embodiment, r is 6 to 10. In somefurther related embodiment, r is 7 to 10. In some further relatedembodiment, r is 8 to 10. In some further related embodiment, r is 9 to10. Moreover, in still further related embodiments, r is 0. In stillsome further embodiment, s is 1 to 10. In still some further embodiment,s is 2 to 10. In still some further embodiment, s is 3 to 10. In stillsome further embodiment, s is 4 to 10. In still some further embodiment,s is 5 to 10. In still some further embodiment, s is 6 to 10. In stillsome further embodiment, s is 7 to 10. In still some further embodiment,s is 8 to 10. In still some further embodiment, s is 9 to 10. R^(1A),R^(1B) and R² may be any of the embodiments described above (e.g.,R^(1A) and R^(1B) maybe isopropyl, R² maybe hydrogen or unsubstitutedC₁-C₂ alkyl).

In some embodiment, q is 0 to 8. In some related embodiment, q is 1 to8. In some related embodiment, q is 2 to 8. In some related embodiment,q is 3 to 8. In some related embodiment, q is 4 to 8. In some relatedembodiment, q is 5 to 8. In some related embodiment, q is 6 to 8. Insome related embodiment, q is 7 to 8. Moreover, in still further relatedembodiments, q is 0. In some further related embodiment, r is 0 to 10.In some further related embodiment, r is 1 to 10. In some furtherrelated embodiment, r is 2 to 10. In some further related embodiment, ris 3 to 10. In some further related embodiment, r is 4 to 10. In somefurther related embodiment, r is 5 to 10. In some further relatedembodiment, r is 6 to 10. In some further related embodiment, r is 7 to10. In some further related embodiment, r is 8 to 10. In some furtherrelated embodiment, r is 9 to 10. Moreover, in still further relatedembodiments, r is 0. In still some further embodiment, s is 1 to 10. Instill some further embodiment, s is 2 to 10. In still some furtherembodiment, s is 3 to 10. In still some further embodiment, s is 4 to10. In still some further embodiment, s is 5 to 10. In still somefurther embodiment, s is 6 to 10. In still some further embodiment, s is7 to 10. In still some further embodiment, s is 8 to 10. In still somefurther embodiment, s is 9 to 10. R^(1A), R^(1B) and R² may be any ofthe embodiments described above (e.g., R^(1A) and R^(1B) maybeisopropyl, R² maybe hydrogen or unsubstituted C₁-C₂ alkyl).

In some embodiment, q is 0 to 7. In some related embodiment, q is 1 to7. In some related embodiment, q is 2 to 7. In some related embodiment,q is 3 to 7. In some related embodiment, q is 4 to 7. In some relatedembodiment, q is 5 to 7. In some related embodiment, q is 6 to 7.Moreover, in still further related embodiments, q is 0. In some furtherrelated embodiment, r is 0 to 10. In some further related embodiment, ris 1 to 10. In some further related embodiment, r is 2 to 10. In somefurther related embodiment, r is 3 to 10. In some further relatedembodiment, r is 4 to 10. In some further related embodiment, r is 5 to10. In some further related embodiment, r is 6 to 10. In some furtherrelated embodiment, r is 7 to 10. In some further related embodiment, ris 8 to 10. In some further related embodiment, r is 9 to 10. Moreover,in still further related embodiments, r is 0. In still some furtherembodiment, s is 1 to 10. In still some further embodiment, s is 2 to10. In still some further embodiment, s is 3 to 10. In still somefurther embodiment, s is 4 to 10. In still some further embodiment, s is5 to 10. In still some further embodiment, s is 6 to 10. In still somefurther embodiment, s is 7 to 10. In still some further embodiment, s is8 to 10. In still some further embodiment, s is 9 to 10. R^(1A), R^(1B)and R² may be any of the embodiments described above (e.g., R^(1A) andR^(1B) maybe isopropyl, R² maybe hydrogen or unsubstituted C₁-C₂ alkyl).

In some embodiment, q is 0 to 6. In some related embodiment, q is 1 to6. In some related embodiment, q is 2 to 6. In some related embodiment,q is 3 to 6. In some related embodiment, q is 4 to 6. In some relatedembodiment, q is 5 to 6. Moreover, in still further related embodiments,q is 0. In some further related embodiment, r is 0 to 10. In somefurther related embodiment, r is 1 to 10. In some further relatedembodiment, r is 2 to 10. In some further related embodiment, r is 3 to10. In some further related embodiment, r is 4 to 10. In some furtherrelated embodiment, r is 5 to 10. In some further related embodiment, ris 6 to 10. In some further related embodiment, r is 7 to 10. In somefurther related embodiment, r is 8 to 10. In some further relatedembodiment, r is 9 to 10. Moreover, in still further relatedembodiments, r is 0. In still some further embodiment, s is 1 to 10. Instill some further embodiment, s is 2 to 10. In still some furtherembodiment, s is 3 to 10. In still some further embodiment, s is 4 to10. In still some further embodiment, s is 5 to 10. In still somefurther embodiment, s is 6 to 10. In still some further embodiment, s is7 to 10. In still some further embodiment, s is 8 to 10. In still somefurther embodiment, s is 9 to 10. R^(1A), R^(1B) and R² may be any ofthe embodiments described above (e.g., R^(1A) and R^(1B) maybeisopropyl, R² maybe hydrogen or unsubstituted C₁-C₂ alkyl).

In some embodiment, q is 0 to 5. In some related embodiment, q is 1 to5. In some related embodiment, q is 2 to 5. In some related embodiment,q is 3 to 5. In some related embodiment, q is 4 to 5. Moreover, in stillfurther related embodiments, q is 0. In some further related embodiment,r is 0 to 10. In some further related embodiment, r is 1 to 10. In somefurther related embodiment, r is 2 to 10. In some further relatedembodiment, r is 3 to 10. In some further related embodiment, r is 4 to10. In some further related embodiment, r is 5 to 10. In some furtherrelated embodiment, r is 6 to 10. In some further related embodiment, ris 7 to 10. In some further related embodiment, r is 8 to 10. In somefurther related embodiment, r is 9 to 10. Moreover, in still furtherrelated embodiments, r is 0. In still some further embodiment, s is 1 to10. In still some further embodiment, s is 2 to 10. In still somefurther embodiment, s is 3 to 10. In still some further embodiment, s is4 to 10. In still some further embodiment, s is 5 to 10. In still somefurther embodiment, s is 6 to 10. In still some further embodiment, s is7 to 10. In still some further embodiment, s is 8 to 10. In still somefurther embodiment, s is 9 to 10. R^(1A), R^(1B) and R² may be any ofthe embodiments described above (e.g., R^(1A) and R^(1B) maybeisopropyl, R² maybe hydrogen or unsubstituted C₁-C₂ alkyl).

In some embodiment, q is 0 to 4. In some related embodiment, q is 1 to4. In some related embodiment, q is 2 to 4. In some related embodiment,q is 3 to 4. Moreover, in still further related embodiments, q is 0. Insome further related embodiment, r is 0 to 10. In some further relatedembodiment, r is 1 to 10. In some further related embodiment, r is 2 to10. In some further related embodiment, r is 3 to 10. In some furtherrelated embodiment, r is 4 to 10. In some further related embodiment, ris 5 to 10. In some further related embodiment, r is 6 to 10. In somefurther related embodiment, r is 7 to 10. In some further relatedembodiment, r is 8 to 10. In some further related embodiment, r is 9 to10. Moreover, in still further related embodiments, r is 0. In stillsome further embodiment, s is 1 to 10. In still some further embodiment,s is 2 to 10. In still some further embodiment, s is 3 to 10. In stillsome further embodiment, s is 4 to 10. In still some further embodiment,s is 5 to 10. In still some further embodiment, s is 6 to 10. In stillsome further embodiment, s is 7 to 10. In still some further embodiment,s is 8 to 10. In still some further embodiment, s is 9 to 10. R^(1A),R^(1B) and R² may be any of the embodiments described above (e.g.,R^(1A) and R^(1B) maybe isopropyl, R² maybe hydrogen or unsubstitutedC₁-C₂ alkyl).

In some embodiment, q is 0 to 3. In some related embodiment, q is 1 to3. In some related embodiment, q is 2 to 3. Moreover, in still furtherrelated embodiments, q is 0. In some further related embodiment, r is 0to 10. In some further related embodiment, r is 1 to 10. In some furtherrelated embodiment, r is 2 to 10. In some further related embodiment, ris 3 to 10. In some further related embodiment, r is 4 to 10. In somefurther related embodiment, r is 5 to 10. In some further relatedembodiment, r is 6 to 10. In some further related embodiment, r is 7 to10. In some further related embodiment, r is 8 to 10. In some furtherrelated embodiment, r is 9 to 10. Moreover, in still further relatedembodiments, r is 0. In still some further embodiment, is 1 to 10. Instill some further embodiment, s is 2 to 10. In still some furtherembodiment, s is 3 to 10. In still some further embodiment, s is 4 to10. In still some further embodiment, s is 5 to 10. In still somefurther embodiment, s is 6 to 10. In still some further embodiment, s is7 to 10. In still some further embodiment, s is 8 to 10. In still somefurther embodiment, s is 9 to 10. R^(1A), R^(1B) and R² may be any ofthe embodiments described above (e.g., R^(1A) and R^(1B) maybeisopropyl, R² maybe hydrogen or unsubstituted C₁-C₂ alkyl).

In some embodiment, q is 0 to 2. In some related embodiment, q is 1 to2. Moreover, in still further related embodiments, q is 0. In somefurther related embodiment, r is 0 to 10. In some further relatedembodiment, r is 1 to 10. In some further related embodiment, r is 2 to10. In some further related embodiment, r is 3 to 10. In some furtherrelated embodiment, r is 4 to 10. In some further related embodiment, ris 5 to 10. In some further related embodiment, r is 6 to 10. In somefurther related embodiment, r is 7 to 10. In some further relatedembodiment, r is 8 to 10. In some further related embodiment, r is 9 to10. Moreover, in still further related embodiments, r is 0. In stillsome further embodiment, s is 1 to 10. In still some further embodiment,s is 2 to 10. In still some further embodiment, s is 3 to 10. In stillsome further embodiment, s is 4 to 10. In still some further embodiment,s is 5 to 10. In still some further embodiment, s is 6 to 10. In stillsome further embodiment, s is 7 to 10. In still some further embodiment,s is 8 to 10. In still some further embodiment, s is 9 to 10R^(1A),R^(1B) and R² may be any of the embodiments described above (e.g.,R^(1A) and R^(1B) maybe isopropyl, R² maybe hydrogen or unsubstitutedC₁-C₂ alkyl).

In some embodiments of the compound of formula (I), or embodimentsthereof provided herein, where R^(1A) and R^(1B) are isopropyl, and R²is hydrogen, the symbol n is 1 or 3. In other embodiments, where R^(1A)is hydrogen, R^(1B) has the structure of formula (IA) and R² ishydrogen, the symbol n is 1 or 3. In some embodiments, where R^(1A) ishydrogen, R^(1B) has the structure of formula (IB) and R² is hydrogen,the symbol n is 1 or 3. In some embodiments, where R^(1A) is hydrogen,R^(1B) has the structure of formula (IC) and R² is hydrogen, the symboln is 1 or 3. In some embodiments, where R^(1A) has the formula ofstructure (IC), R^(1B) has the structure of formula (ID) and R² ishydrogen, the symbol n is 1 or 3. In some embodiments, where R^(1A) andR^(1B) have the formula of structure (ID) and R² is hydrogen, the symboln is 1 or 3. In other embodiments, where R^(1A) is hydrogen, R^(1B) isphenyl and R² is hydrogen, the symbol n is 1 or 3. In other embodiments,where R^(1A) is hydrogen, R^(1B) is 6 membered cycloalkyl and R² ishydrogen, the symbol n is 1 or 3.

In some embodiments, the co-solvent is a compound having the formula(I). In some embodiments, R^(1A) and R^(1B) are isopropyl, R² ishydrogen, and the symbol n is 1. In some related embodiments, theco-solvent is present at about 2% (w/v). The compound of formula (I),wherein R^(1A) and R^(1B) are isopropyl, R² is hydrogen, and the symboln is 1 may be referred to herein as DIPA-1EO. In some embodiments,R^(1A) and R^(1B) are isopropyl, R² is hydrogen, and the symbol n is 3.In some related embodiments, the co-solvent is present at about 0.5%(w/v). The compound of formula (I), wherein R^(1A) and R^(1B) areisopropyl, R² is hydrogen, and the symbol n is 3 may be referred toherein as DIPA-3EO.

In some embodiments, the co-solvent is a compound having the formula(I). In some embodiments, R^(1A) and R^(1B) are isopropyl, R² ishydrogen, and the symbol n is 15. In some related embodiments, theco-solvent is present at about 1.5% (w/v). In some related embodiments,the co-solvent is present at about 2% (w/v). In some relatedembodiments, the co-solvent is present at about 2.5% (w/v). In somerelated embodiments, the co-solvent is present at about 3% (w/v). Insome related embodiments, the co-solvent is present at about 3.5% (w/v).The compound of formula (I), wherein R^(1A) and R^(1B) are isopropyl, R²is hydrogen, and the symbol n is 15 may be referred to herein asDIPA-15EO.

In other embodiments, the co-solvent is an alkylamine. In someembodiments, the alkylamine is diisopropylamine. In other embodiments,the alkylamine is an alkylpolyamine. In some embodiments, thealkylpolyamine is dimethylaminopropylamine, triethylenetetramine ordiethylenetriamine. In some embodiments, the alkylpolyamine isdimethylaminopropylamine. In other embodiments, the alkylpolyamine istriethylenetetramine. In some embodiments, the alkylpolyamine isdiethylenetriamine. Diisopropylamine (DIPA) refers to, in the customarysense, CAS Registry No 108-18-9. Dimethylaminopropylamine (DMAPA) refersto, in the customary sense, CAS Registry No. 109-55-7.Triethylenetetramine (TETA) refers to, in the customary sense, CASRegistry No. 112-24-3. Diethylenetriamine (DETA) refers to, in thecustomary sense, CAS Registry No. 111-40-0. In some embodiments, theco-solvent is an arylamine. In some embodiments, the arylamine isaniline. In embodiments, DMAPA is present at about 2% (w/v). Inembodiments, TETA is present at about 2% (w/v).

As described above the emulsion composition provided herein includes aheavy crude oil, water, and a co-solvent, wherein the co-solvent is analkylamine or a compound having the formula (I). In one embodiment, theemulsion composition includes a heavy crude oil, water and analkylamine, wherein the alkylamine is triethylenetetramine, present at2% (w/v). In one embodiment, the emulsion composition includes a heavycrude oil, water and an alkylamine, wherein the alkylamine istriethylenetetramine, present at 1% (w/v). In one embodiment, theemulsion composition includes a heavy crude oil, water and analkylamine, wherein the alkylamine is dimethylaminopropylamine, presentat 2% (w/v). In another embodiment, the emulsion composition includes aheavy crude oil, water and a compound of formula (I), wherein R^(1A) andR^(1B) are isopropyl, R² is hydrogen, and the symbol n is 1, present atabout 2% (w/v). In another embodiment, the emulsion composition includesa heavy crude oil, water and a compound of formula (I), wherein R^(1A)and R^(1B) are isopropyl, R² is hydrogen, and the symbol n is 3, presentat about 0.5% (w/v).

In one embodiment, where the emulsion composition includes a heavy crudeoil, water and an alkylamine, the emulsion composition does not includea compound having the formula (I), (II) or (III). In some relatedembodiments, the alkylamine is triethylenetetramine. In other relatedembodiments, the alkylamine is dimethylaminopropylamine.

In one embodiment, where the emulsion composition includes a heavy crudeoil, water and a co-solvent (e.g., an alkylamine or a compound offormula (I), (II), or (III)), the emulsion composition does not includea surfactant.

As described above, the emulsion composition provided herein may includea heavy crude oil, water and a co-solvent (e.g., an alkyamine or acompound of formula (I), (II), or (III)). In one embodiment, where theemulsion composition includes a heavy crude oil, water and a co-solvent(e.g., an alkylamine or a compound of formula (I), (II), or (III)), theemulsion composition does not include an alkali agent. In some relatedembodiments, the co-solvent is a basic co-solvent.

The emulsion composition provided herein includes a co-solvent offormula (I). In embodiments, the emulsion includes an additionalco-solvent. Where the emulsion includes an additional co-solvent theco-solvent and the additional co-solvent form a co-solvent blend (e.g. aplurality of co-solvent types). Thus, in embodiments, the co-solvent isa single co-solvent type (e.g., a compound of formula (I)) in theemulsion. An “additional co-solvent” as provided herein is anyco-solvent useful in enhanced oil recovery and transport of heavy oil(e.g., compounds of the formula (IV) or (V) as provided herein). Inembodiments, the co-solvent is a co-solvent blend. A “co-solvent blend”as provided herein is a mixture of a plurality of co-solvent types(e.g., a compound of formula (I) and one or more additional co-solvent).Thus, in one embodiment, the emulsion composition includes a pluralityof different co-solvents (e.g., a compound of formula (I) and one ormore additional co-solvents). Where the emulsion composition includes aplurality of different co-solvents, the different co-solvents can bedistinguished by their chemical (structural) properties. For example,the emulsion composition may include a co-solvent having the structureof formula (I) and an additional co-solvent, wherein the co-solvent andthe additional co-solvent are chemically different. The emulsioncomposition may include a co-solvent having the structure of formula (I)and a first additional co-solvent, a second additional co-solvent and athird additional co-solvent, wherein the first additional co-solvent ischemically different from the second and the third additionalco-solvent, and the second additional co-solvent is chemically differentfrom the third additional co-solvent. In one embodiment, the co-solventblend includes a compound of formula (I) and at least two differentalcohols (e.g. a C₁-C₆ alcohol and a C₁-C₄ alcohol). In one embodiment,the emulsion composition includes a compound of formula (I) and a C₁-C₆alcohol and a C₁-C₄ alcohol. In other embodiments, the co-solvent blendincludes a compound of formula (I) and at least two different alkoxyalcohols (e.g. a C₁-C₆ alkoxy alcohol and a C₁-C₄ alkoxy alcohol). Inother embodiments, the emulsion composition includes a compound offormula (I) and a C₁-C₆ alkoxy alcohol and a C₁-C₄ alkoxy alcohol. Inembodiments, the emulsion composition includes a compound of formula(I), (II) or (III) and a phenol alkoxy alcohol. In one embodiment, theco-solvent blend includes a compound of formula (I), (II) or (III) andat least two co-solvents selected from the group consisting of alcohols,alkyl alkoxy alcohols and phenyl alkoxy alcohols. For example, theco-solvent blend may include a compound of formula (I), (II) or (III)and an alcohol, an alkyl alkoxy alcohol or a phenyl alkoxy alcohol. Thealkyl alkoxy alcohols or phenyl alkoxy alcohols provided herein have ahydrophobic portion (alkyl or aryl chain), a hydrophilic portion (e.g.an alcohol) and optionally an alkoxy (ethoxylate or propoxylate)portion.

In embodiments, the emulsion compositions provided herein include anadditional co-solvent. The additional co-solvent may form part of aco-solvent blend together with a compound of formula (I), (II) or (III).In embodiments, the additional co-solvent has the formula

In formula (IV), L¹ is unsubstituted C₁-C₆ alkylene, unsubstitutedphenylene, unsubstituted cyclohexylene, unsubstituted cyclopentylene ormethyl-substituted cyclopentylene. R² is independently hydrogen, methylor ethyl. R³ is independently hydrogen or

R⁴ is independently hydrogen, methyl or ethyl, n is an integer from 0 to30, and m is an integer from 0 to 30. In one embodiment, n is an integerfrom 0 to 25. In one embodiment, n is an integer from 0 to 20. In oneembodiment, n is an integer from 0 to 15. In one embodiment, n is aninteger from 0 to 10. In one embodiment, n is an integer from 0 to 5. Inone embodiment, n is 1. In other embodiments, n is 3. In one embodiment,n is 5. In one embodiment, m is an integer from 0 to 25. In oneembodiment, m is an integer from 0 to 20. In one embodiment, m is aninteger from 0 to 15. In one embodiment, m is an integer from 0 to 10.In one embodiment, m is an integer from 0 to 5. In one embodiment, mis 1. In other embodiments, m is 3. In one embodiment, m is 5. Informula (IV) each of R² and R⁴ can appear more than once and can beoptionally different. For example, in one embodiment where n is 2, R²appears twice and can be optionally different. In other embodiments,where m is 3, R⁴ appears three times and can be optionally different.

L¹ may be linear or branched unsubstituted alkylene. In one embodiment,L¹ of formula (IV) is linear unsubstituted C₁-C₆ alkylene. In oneembodiment, L¹ of formula (IV) is branched unsubstituted C₁-C₆ alkylene.In other embodiments, L¹ of formula (IV) is linear unsubstituted C₂-C₆alkylene. In other embodiments, L¹ of formula (IV) is branchedunsubstituted C₂-C₆ alkylene. In other embodiments, L¹ of formula (IV)is linear unsubstituted C₃-C₆ alkylene. In other embodiments, L¹ offormula (IV) is branched unsubstituted C₃-C₆ alkylene. In otherembodiments, L¹ of formula (IV) is linear unsubstituted C₄-C₆ alkylene.In other embodiments, L¹ of formula (IV) is branched unsubstituted C₄-C₆alkylene. In other embodiments, L¹ of formula (IV) is linearunsubstituted C₄-alkylene. In other embodiments, L¹ of formula (IV) isbranched unsubstituted C₄-alkylene.

In one embodiment, where L¹ is linear or branched unsubstituted alkylene(e.g. branched unsubstituted C₁-C₆ alkylene), the alkylene is asaturated alkylene (e.g. a linear or branched unsubstituted saturatedalkylene or branched unsubstituted C₁-C₆ saturated alkylene). A“saturated alkylene,” as used herein, refers to an alkylene consistingonly of hydrogen and carbon atoms that are bonded exclusively by singlebonds. Thus, in one embodiment, L¹ is linear or branched unsubstitutedsaturated alkylene. In one embodiment, L¹ of formula (IV) is linearunsubstituted saturated C₁-C₆ alkylene. In one embodiment, L¹ of formula(IV) is branched unsubstituted saturated C₁-C₆ alkylene. In otherembodiments, L¹ of formula (IV) is linear unsubstituted saturated C₂-C₆alkylene. In other embodiments, L¹ of formula (IV) is branchedunsubstituted saturated C₂-C₆ alkylene. In other embodiments, L¹ offormula (IV) is linear unsubstituted saturated C₃-C₆ alkylene. In otherembodiments, L¹ of formula (IV) is branched unsubstituted saturatedC₃-C₆ alkylene. In other embodiments, L¹ of formula (IV) is linearunsubstituted saturated C₄-C₆ alkylene. In other embodiments, L¹ offormula (IV) is branched unsubstituted saturated C₄-C₆ alkylene. Inother embodiments, L¹ of formula (IV) is linear unsubstituted saturatedC₄-alkylene. In other embodiments, L¹ of formula (IV) is branchedunsubstituted saturated C₄-alkylene.

In one embodiment, L¹ of formula (IV) is substituted or unsubstitutedcycloalkylene or unsubstituted arylene. In one embodiment, L¹ of formula(IV) is R⁷-substituted or unsubstituted cyclopropylene, wherein R⁷ isC₁-C₃ alkyl. In other embodiments, L¹ of formula (IV) is R⁸-substitutedor unsubstituted cyclobutylene, wherein R⁸ is C₁-C₂ alkyl. In otherembodiments, L¹ of formula (IV) is R⁹-substituted or unsubstitutedcyclopentylene, wherein R⁹ is C₁-alkyl. In other embodiments, L¹ offormula (IV) is R¹⁰-substituted or unsubstituted cyclopentylene, whereinR¹⁰ is unsubstituted cyclohexyl. In one embodiment, L¹ of formula (IV)is unsubstituted phenylene, unsubstituted cyclohexylene, unsubstitutedcyclopentylene or methyl-substituted cyclopentylene.

In one embodiment, -L¹-R³ of formula (IV) is C₁-C₆ alkyl, unsubstitutedphenyl, unsubstituted cyclohexyl, unsubstituted cyclopentyl or amethyl-substituted cycloalkyl.

In one embodiment, the additional co-solvent has the structure offormula

In formula (IVA), R¹¹ is C₁-C₆ alkyl, unsubstituted phenyl,unsubstituted cyclohexyl, unsubstituted cyclopentyl or amethyl-substituted cycloalkyl.

In one embodiment, n and m are independently 1 to 20. In otherembodiments, n and m are independently 1 to 15. In other embodiments, nand m are independently 1 to 10. In one embodiment, n and m areindependently 1 to 6. In one embodiment, n and m are independently 1.

The additional co-solvent included in the emulsion compositions providedherein may be a monohydric or a dihydric alkoxy alcohol (e.g. C₁-C₆alkoxy alcohol or C₁-C₆ alkoxy diol). Where the additional co-solvent isa monohydric alcohol, the co-solvent has the formula (IV) and R³ ishydrogen. Where the additional co-solvent is a diol, the co-solvent hasthe formula (IV) and R³ is

In one embodiment, L¹ is linear unsubstituted C₄ alkylene and n is 3. Inone embodiment, the additional co-solvent is triethylene glycol butylether. In other embodiments, the additional co-solvent is tetraethyleneglycol. In further embodiments, m is 3. In one embodiment, L¹ is linearunsubstituted C₄ alkylene and n is 5. In one embodiment, the additionalco-solvent is pentaethylene glycol n-butyl ether. In furtherembodiments, m is 5. In one embodiment, L¹ is branched unsubstituted C₄alkylene and n is 1. In one embodiment, the additional co-solvent isethylene glycol iso-butyl ether. In further embodiments, m is 1. In oneembodiment, L¹ is branched unsubstituted C₄ alkylene and n is 3. In oneembodiment, the additional co-solvent is triethylene glycol iso-butylether. In further embodiments, m is 3. In one embodiment, the additionalco-solvent is ethylene glycol or propylene glycol. In other embodiments,the additional co-solvent is ethylene glycol alkoxylate or propyleneglycol alkoxylate. In one embodiment, the additional co-solvent ispropylene glycol diethoxylate or propylene glycoltriethoxylate. In oneembodiment, the additional co-solvent is propylene glycoltetraethoxylate. In some embodiments, the additional co-solvent is analcohol, alkoxy alcohol, glycol ether, glycol or glycerol. Inembodiments, the additional co-solvent is an alcohol, alkoxy alcohol orglycol ether.

In the structure of formula (IV), R³ may be hydrogen or

Thus in one embodiment, R³ is

In one embodiment, the additional co-solvent provided herein may be analcohol or diol (C₁-C₆ alcohol or C₁-C₆ diol). Where the additionalco-solvent is an alcohol, the co-solvent has a structure of formula(IV), where R³ is hydrogen and n is 0. Where the additional co-solventis a diol, the co-solvent has a structure of formula (IV), where R³ is

and n and m are 0. Thus, in one embodiment, n and m are independently 0.In one embodiment, L¹ is linear or branched unsubstituted C₁-C₆alkylene. In other embodiments, L¹ is linear or branched unsubstitutedC₂-C₆ alkylene. In one embodiment, L¹ is linear or branchedunsubstituted C₂-C₆ alkylene. In one embodiment L¹ is linear or branchedunsubstituted C₃-C₆ alkylene. In other embodiments, L¹ is linear orbranched unsubstituted C₄-C₆ alkylene. In one embodiment, L¹ is linearor branched unsubstituted C₄-alkylene. In one embodiment, L¹ is branchedunsubstituted butylene. In one embodiment, the additional co-solvent hasthe structure of formula

In other embodiments, the additional co-solvent has the structure offormula

In one embodiment, the additional co-solvent has the structure offormula

In some embodiments, the additional co-solvent has the formula

In formula (V) R¹ is independently hydrogen, unsubstituted C₁-C₆ alkylor R⁵—OH, R² is independently hydrogen or unsubstituted C₁-C₂ alkyl, R⁵is independently a bond or unsubstituted C₁-C₆ alkyl, n is an integerfrom 1 to 30, o is an integer from 1 to 5 and z is an integer from 1 to5. In some embodiments, R¹ is unsubstituted C₂-C₆ alkyl. In someembodiments, R¹ is unsubstituted C₄-C₆ alkyl. In some embodiments, R¹ isunsubstituted C₁-C₅ alkyl. In other embodiments, R¹ is unsubstitutedC₁-C₄ alkyl. In other embodiments, R¹ is unsubstituted C₁-C₃ alkyl. Insome embodiments, R¹ is unsubstituted C₁-C₂ alkyl. In some embodiments,R¹ is unsubstituted C₂ alkyl. In other embodiments, R¹ is ethyl. In someembodiments, R¹ is methyl. In some embodiment, R¹ is hydrogen.

In some embodiment, R¹ is independently a bond or R⁵—OH. In someembodiment, R¹ is R⁵—OH. In some embodiments, R⁵ is unsubstituted C₂-C₆alkyl. In some embodiments, R⁵ is unsubstituted C₄-C₆ alkyl. In someembodiments, R⁵ is unsubstituted C₁-C₅ alkyl. In other embodiments, R⁵is unsubstituted C₁-C₄ alkyl. In other embodiments, R⁵ is unsubstitutedC₁-C₃ alkyl. In some embodiments, R⁵ is unsubstituted C₁-C₂ alkyl. Insome embodiments, R⁵ is unsubstituted C₂ alkyl. In other embodiments, R⁵is ethyl. In some embodiments, R⁵ is methyl. In some embodiments, R⁵ isa bond.

In formula (V) the symbol n is an integer from 1 to 30. In oneembodiment, n is an integer from 1 to 25. In one embodiment, n is aninteger from 1 to 20. In one embodiment, n is an integer from 1 to 15.In one embodiment, n is an integer from 1 to 10. In one embodiment, n isan integer from 1 to 5. In some embodiment, n is 1, 2, 3, 4, 5, 6, 7, 8,9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, 22, 23, 24, 25, 26,27, 28, 29, or 30. In one embodiment, n is 3. In other embodiments, n is5. In one embodiment, n is 6. In one embodiment, n is 16.In formula (V) the symbol o is an integer from 1 to 5 and the symbol zis an integer from 1 to 5. In embodiments, o is 1, 2, 3, 4, or 5. Inembodiments, z is 1, 2, 3, 4, or 5. In embodiments, o is 1 and z is 5.In further embodiments, R¹ is independently hydrogen or R⁵—OH and R⁵ isa bond. In other further embodiments, R¹ is hydrogen. In other furtherembodiments, R¹ is R⁵—OH and R⁵ is a bond.

In some embodiments, the additional co-solvent has the formula

In formula (VA) R¹ is independently hydrogen or unsubstituted C₁-C₆alkyl, R² is independently hydrogen or unsubstituted C₁-C₂ alkyl and nis an integer from 1 to 30. In some embodiments, R¹ is unsubstitutedC₂-C₆ alkyl. In some embodiments, R¹ is unsubstituted C₄-C₆ alkyl. Insome embodiments, R¹ is unsubstituted C₁-C₅ alkyl. In other embodiments,R¹ is unsubstituted C₁-C₄ alkyl. In other embodiments, R¹ isunsubstituted C₁-C₃ alkyl. In some embodiments, R¹ is unsubstitutedC₁-C₂ alkyl. In some embodiments, R¹ is unsubstituted C₂ alkyl. In otherembodiments, R¹ is ethyl. In some embodiments, R¹ is methyl. In someembodiment, R¹ is hydrogen.

R¹ may be linear or branched unsubstituted alkyl. In one embodiment, R¹of formula (VA) is linear unsubstituted C₁-C₆ alkyl. In one embodiment,R¹ of formula (VA) is branched unsubstituted C₁-C₆ alkyl. In otherembodiments, R¹ of formula (VA) is linear unsubstituted C₁-C₅ alkyl. Inother embodiments, R¹ of formula (VA) is branched unsubstituted C₁-C₅alkyl. In other embodiments, R¹ of formula (VA) is linear unsubstitutedC₁-C₄ alkyl. In other embodiments, R¹ of formula (VA) is branchedunsubstituted C₁-C₄ alkyl. In other embodiments, R¹ of formula (VA) islinear unsubstituted C₁-C₃ alkyl. In other embodiments, R¹ of formula(VA) is branched unsubstituted C₁-C₃ alkyl. In other embodiments, R¹ offormula (VA) is linear unsubstituted ethyl. In other embodiments, R¹ offormula (VA) is branched unsubstituted ethyl.

In one embodiment, where R¹ is linear or branched unsubstituted alkyl(e.g. branched unsubstituted C₁-C₆ alkyl), the alkyl is a saturatedalkyl (e.g. a linear or branched unsubstituted saturated alkyl orbranched unsubstituted C₁-C₆ saturated alkyl). A “saturated alkyl,” asused herein, refers to an alkyl consisting only of hydrogen and carbonatoms that are bonded exclusively by single bonds. Thus, in oneembodiment, R¹ is linear or branched unsubstituted saturated alkyl. Inone embodiment, R¹ of formula (VA) is linear unsubstituted saturatedC₁-C₆ alkyl. In one embodiment, R¹ of formula (VA) is branchedunsubstituted saturated C₁-C₆ alkyl. In other embodiments, R¹ of formula(VA) is linear unsubstituted saturated C₁-C₅ alkyl. In otherembodiments, R¹ of formula (VA) is branched unsubstituted saturatedC₁-C₅ alkyl. In other embodiments, R¹ of formula (VA) is linearunsubstituted saturated C₁-C₄ alkyl. In other embodiments, R¹ of formula(VA) is branched unsubstituted saturated C₁-C₄ alkyl. In otherembodiments, R¹ of formula (VA) is linear unsubstituted saturated C₁-C₃alkyl. In other embodiments, R¹ of formula (VA) is branchedunsubstituted saturated C₁-C₃ alkyl. In other embodiments, R¹ of formula(VA) is linear unsubstituted saturated ethyl. In other embodiments, R¹of formula (VA) is branched unsubstituted saturated ethyl.

In formula (VA) the symbol n is an integer from 1 to 30. In oneembodiment, n is an integer from 1 to 25. In one embodiment, n is aninteger from 1 to 20. In one embodiment, n is an integer from 1 to 15.In one embodiment, n is an integer from 1 to 10. In one embodiment, n isan integer from 1 to 5. In some embodiment, n is 1, 2, 3, 4, 5, 6, 7, 8,9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, 22, 23, 24, 25, 26,27, 28, 29, or 30. In one embodiment, n is 3. In other embodiments, n is5. In one embodiment, n is 6. In one embodiment, n is 16.

In some embodiments, R¹ is hydrogen. In other related embodiments, n isas defined in an embodiment above (e.g. n is at least 1, or at least 15,e.g. 5 to 20). Thus, in some embodiments, R¹ is hydrogen and n is 16.

In some embodiments, R¹ is methyl. In other related embodiments, n is asdefined in an embodiment above (e.g. n is at least 1, or at least 10,e.g. 5 to 20). Thus, in some embodiments, R¹ is methyl and n is 16.

In some embodiment, the additional co-solvent has the formula:

In formula (VB) R¹ is defined as above (e.g. unsubstituted C₁-C₆ alkyl),R² is methyl or ethyl, o is an integer from 0 to 10 and p is an integerfrom 1 to 20. In some embodiments, R² is methyl. In other embodiments,R² is ethyl. In formula (VB) R² can appear more than once and can beoptionally different. For example, in some embodiments where o is 3, R²appears three times and can be optionally different. In otherembodiments, where o is 6, R² appears six times and can be optionallydifferent.

In some embodiments, o is 0 to 10. In some related embodiments, o is 0to 8. In some related embodiments, o is 0 to 6. In some relatedembodiments, o is 0 to 4. In some related embodiments, o is 0 to 2. Instill further related embodiments, o is 0. In some further relatedembodiment, p is 1 to 20. In some further related embodiment, p is 1 to18. In some further related embodiment, p is 1 to 16. In some furtherrelated embodiment, p is 1 to 14. In some further related embodiment, pis 1 to 12. In some further related embodiment, p is 1 to 10. In somefurther related embodiment, p is 1 to 8. In some further relatedembodiment, p is 1 to 6. In some further related embodiment, p is 1 to4. In some further related embodiment, p is 1 to 2. In still somefurther related embodiment, p is more than 1. In some furtherembodiment, p is 6. In some further embodiment, p is 16. R¹ and R² maybe any of the embodiments described above (e.g. R¹ maybe linearunsubstituted C₁-C₆ alkyl, R² maybe linear unsubstituted C₁-C₂ alkyl).Thus, in some embodiment, R¹ is hydrogen, o is 0 and p is 16.

In some embodiments, o is 1 to 10. In some related embodiments, o is 1to 8. In some related embodiments, o is 1 to 6. In some relatedembodiments, o is 1 to 4. In some related embodiments, o is 1 to 2. Insome further related embodiment, p is 1 to 20. In some further relatedembodiment, p is 1 to 18. In some further related embodiment, p is 1 to16. In some further related embodiment, p is 1 to 14. In some furtherrelated embodiment, p is 1 to 12. In some further related embodiment, pis 1 to 10. In some further related embodiment, p is 1 to 8. In somefurther related embodiment, p is 1 to 6. In some further relatedembodiment, p is 1 to 4. In some further related embodiment, p is 1 to2. In still some further related embodiment, p is more than 1. R¹ and R²may be any of the embodiments described above (e.g. R¹ maybe linearunsubstituted C₁-C₆ alkyl, R² maybe linear unsubstituted C₁-C₂ alkyl).

In some embodiments, o is 2 to 10. In some related embodiments, o is 2to 8. In some related embodiments, o is 2 to 6. In some relatedembodiments, o is 2 to 4. In some further related embodiment, p is 1 to20. In some further related embodiment, p is 1 to 18. In some furtherrelated embodiment, p is 1 to 16. In some further related embodiment, pis 1 to 14. In some further related embodiment, p is 1 to 12. In somefurther related embodiment, p is 1 to 10. In some further relatedembodiment, p is 1 to 8. In some further related embodiment, p is 1 to6. In some further related embodiment, p is 1 to 4. In some furtherrelated embodiment, p is 1 to 2. In still some further relatedembodiment, p is more than 1. R¹ and R² may be any of the embodimentsdescribed above (e.g. R¹ maybe linear unsubstituted C₁-C₆ alkyl, R²maybe linear unsubstituted C₁-C₂ alkyl).

In some embodiments, o is 4 to 10. In some related embodiments, o is 4to 8. In some related embodiments, o is 4 to 6. In some further relatedembodiment, p is 1 to 20. In some further related embodiment, p is 1 to18. In some further related embodiment, p is 1 to 16. In some furtherrelated embodiment, p is 1 to 14. In some further related embodiment, pis 1 to 12. In some further related embodiment, p is 1 to 10. In somefurther related embodiment, p is 1 to 8. In some further relatedembodiment, p is 1 to 6. In some further related embodiment, p is 1 to4. In some further related embodiment, p is 1 to 2. In still somefurther related embodiment, p is more than 1. R¹ and R² may be any ofthe embodiments described above (e.g. R¹ maybe linear unsubstitutedC₁-C₆ alkyl, R² maybe linear unsubstituted C₁-C₂ alkyl).

In some embodiments, o is 6 to 10. In some related embodiments, o is 6to 8. In some further related embodiment, p is 1 to 20. In some furtherrelated embodiment, p is 1 to 18. In some further related embodiment, pis 1 to 16. In some further related embodiment, p is 1 to 14. In somefurther related embodiment, p is 1 to 12. In some further relatedembodiment, p is 1 to 10. In some further related embodiment, p is 1 to8. In some further related embodiment, p is 1 to 6. In some furtherrelated embodiment, p is 1 to 4. In some further related embodiment, pis 1 to 2. In still some further related embodiment, p is more than 1.R¹ and R² may be any of the embodiments described above (e.g. R¹ maybelinear unsubstituted C₁-C₆ alkyl, R² maybe linear unsubstituted C₁-C₂alkyl).

In some embodiments, o is 8 to 10. In some further related embodiment, pis 1 to 20. In some further related embodiment, p is 1 to 18. In somefurther related embodiment, p is 1 to 16. In some further relatedembodiment, p is 1 to 14. In some further related embodiment, p is 1 to12. In some further related embodiment, p is 1 to 10. In some furtherrelated embodiment, p is 1 to 8. In some further related embodiment, pis 1 to 6. In some further related embodiment, p is 1 to 4. In somefurther related embodiment, p is 1 to 2. In still some further relatedembodiment, p is more than 1. R¹ and R² may be any of the embodimentsdescribed above (e.g. R¹ maybe linear unsubstituted C₁-C₆ alkyl, R²maybe linear unsubstituted C₁-C₂ alkyl).

In formula (V), (VA) or (VB) R² may be independently hydrogen orunsubstituted C₁-C₂ alkyl. In some embodiments, R² is hydrogen orunsubstituted C₁ or C₂ alkyl. In some related embodiments, R² ishydrogen or branched unsubstituted C₁ or C₂ saturated alkyl. In someembodiments, R² is hydrogen or a branched unsubstituted C₁ saturatedalkyl. In some embodiments, R² is independently hydrogen or methyl. Inother embodiments, R² is independently hydrogen or ethyl. In someembodiments, R² is independently hydrogen, methyl or ethyl. In someembodiments, R² is hydrogen. In some embodiments, R² is methyl. In someembodiments, R² is ethyl. In formula (V) R² can appear more than onceand can be optionally different. For example, in some embodiments wheren is 3, R² appears three times and can be optionally different. In otherembodiments, where n is 6, R² appears six times and can be optionallydifferent.

In some embodiments, where multiple R² substituents are present and atleast two R² substituents are different, R² substituents with the fewestnumber of carbons are present to the side of the compound of formula(V), (VA) or (VB) bound to the —OH group. In this embodiment, thecompound of formula (V), (VA) or (VB) will be increasingly hydrophilicin progressing from the R¹ substituent to the side of the compound offormula (V), (VA) or (VB) bound to the —OH group. The term “side of thecompound of formula ((V), (VA) or (VB) bound to the —OH group” refers tothe side of the compound indicated by asterisks in the below structures:

In some embodiments, R² is hydrogen. In other related embodiments, n isas defined in an embodiment above (e.g. n is at least 1, or at least 20,e.g. 5 to 15). Thus, in some embodiments, R² is hydrogen and n is 16.

In some embodiments, R² is methyl. In other related embodiments, n is asdefined in an embodiment above (e.g. n is at least 1, or at least 20,e.g. 5 to 15). Thus, in some embodiments, R² is methyl and n is 16.

In some embodiment, the additional co-solvent is present from about0.01% w/w to about 5% w/w.

In some embodiment, the total co-solvent concentration (i.e. the totalamount of all co-solvent types within the emulsions and emulsioncompositions provided herein) is from about 0.05% w/w to about 10% w/w.In other embodiments, the total co-solvent concentration in the emulsionis from about 0.25% w/w to about 10% w/w. In other embodiments, thetotal co-solvent concentration in the emulsion is about 0.5% w/w. Inother embodiments, the total co-solvent concentration in the emulsion isabout 1.0% w/w. In other embodiments, the total co-solvent concentrationin the emulsion is about 1.25% w/w. In other embodiments, the totalco-solvent concentration in the emulsion is about 1.5% w/w. In otherembodiments, the total co-solvent concentration in the emulsion is about1.75% w/w. In other embodiments, the total co-solvent concentration inthe emulsion is about 2.0% w/w. In other embodiments, the totalco-solvent concentration in the emulsion is about 2.5% w/w. In otherembodiments, the total co-solvent concentration in the emulsion is about3.0% w/w. In other embodiments, the total co-solvent concentration inthe emulsion is about 3.5% w/w. In other embodiments, the totalco-solvent concentration in the emulsion is about 4.0% w/w. In otherembodiments, the total co-solvent concentration in the emulsion is about4.5% w/w. In other embodiments, the total co-solvent concentration inthe emulsion is about 5.0% w/w. In other embodiments, the totalco-solvent concentration in the emulsion is about 5.5% w/w. In otherembodiments, the total co-solvent concentration in the emulsion is about6.0% w/w. In other embodiments, the total co-solvent concentration inthe emulsion is about 6.5% w/w. In other embodiments, the totalco-solvent concentration in the emulsion is about 7.0% w/w. In otherembodiments, the total co-solvent concentration in the emulsion is about7.5% w/w. In other embodiments, the total co-solvent concentration inthe emulsion is about 8.0% w/w. In other embodiments, the totalco-solvent concentration in the emulsion is about 9.0% w/w. In otherembodiments, the total co-solvent concentration in the emulsion is about10% w/w.

In some embodiments, the emulsion composition includes a plurality ofco-solvents. Where the emulsion composition includes a plurality ofdifferent co-solvents the emulsion composition may include a firstco-solvent, a second co-solvent or a third co-solvent. The first, secondand third co-solvent may be independently different (e.g., a compound offormula (I) and an alkylamine; or two alkylamines having a differenthydrocarbon chain length and different number of nitrogen atoms). Thus,in some embodiments, the first co-solvent is an alkylamine and thesecond co-solvent is a compound having the formula (I). In otherembodiments, the first co-solvent is a triethylenetetramine and thesecond co-solvent is a compound of formula (I), wherein R^(1A) andR^(1B) are isopropyl, R² is hydrogen, and the symbol n is 1. In otherembodiments, the co-solvent is an alkylamine and a compound having theformula (I).

As described above the emulsion composition provided herein may includea co-solvent, wherein the co-solvent is capable of reacting with anunrefined petroleum acid (e.g. the acid in crude oil (reactive oil)) toform soap (a surfactant salt of a fatty acid) in situ. The formation ofsoap in situ promotes the formation of emulsions (both microemulsion andmacroemulsion) providing for efficient decrease of the heavy crude oilviscosity by lowering the interfacial tension between the water and theheavy crude oil.

In some embodiments, the emulsion composition includes a co-solvent(e.g., an alkylamine or a compound of formula (I), (II), or (III)) andan alkali agent. Where the emulsion composition includes a co-solvent(e.g., an alkylamine or a compound of formula (I), (II), or (III)) andan alkali agent, the co-solvent serves as an interfacial viscosityreducing agent when in contact with the heavy crude oil (e.g. anunrefined petroleum) within the heavy crude oil emulsion composition. An“interfacial viscosity reducing agent” as provided herein is an agentthat in the presence of an alkali agent facilitates the formation ofsoap in situ from carboxylic acids (e.g. endogenous carboxylic acids)contained in the unrefined oil (also referred to herein as unrefined oilacid). By contacting the alkali agent with the carboxylic acid in thecrude oil (e.g. by delivering the alkali agent more efficiently thanwater alone) the co-solvent facilitates the generation of soap in situ.The co-solvent provided herein may further allow for the formation of amicroemulsion between the unrefined petroleum, the alkali agent, theco-solvent and the water. The co-solvent may decrease the interfacialviscosity and thus help promote emulsion formation and transform highlyviscous macroemulsions to less viscous microemulsions. The co-solventmay further break the macroemulsions or prevent the formation of highlyviscous macroemulsion entirely. In some embodiments, where the emulsioncomposition includes a co-solvent (e.g., an alkylamine or a compound offormula (I), (II), or (III)) and an alkali agent, the co-solvent iscapable of accepting protons from the carboxylic acid in the crude oil,thereby forming a protonated co-solvent. The alkali agent may acceptprotons from the protonated co-solvent, thereby forming a regeneratedco-solvent. Thus, as an interfacial viscosity reducing agent and as abasic co-solvent, the co-solvent provided herein including embodimentsthereof (e.g., an alkylamine or a compound of formula (I), (II), or(III)), may act to facilitate the transport of the heavy crude oilemulsion composition by decreasing the viscosity and thereby increasingthe flow of heavy crude oil emulsion.

The co-solvents according to the embodiments provided herein may also bereferred to herein as “co-solvents provided herein” or “the co-solventof the present invention.” Any one or combination of a co-solvent (e.g.,an alkylamine or a compound of formula (I), (II), or (III)) is useful inthe methods and compositions provided herein.

In some embodiments, the co-solvent is present in an amount sufficientto decrease the viscosity of the heavy crude oil at least 1,000-fold. Insome embodiments, the co-solvent is present in an amount sufficient todecrease the viscosity of the heavy crude oil at least 1,000-fold. Inother words, in the presence of a sufficient amount of the co-solvent,the viscosity of the heavy crude oil is lowered at least 1,000-foldcompared to the absence of the co-solvent. Thus, in the presence of asufficient amount of the co-solvent the viscosity of the heavy crude oilis lower than in the absence of the co-solvent. In some embodiments, theco-solvent is present in an amount sufficient to decrease the viscosityof the heavy crude oil at least 10,000-fold. In some embodiments, theco-solvent is present in an amount sufficient to decrease the viscosityof the heavy crude oil at least 100,000-fold. In some embodiments, theco-solvent is present in an amount sufficient to decrease the viscosityof the heavy crude oil at least 200,000-fold.

The co-solvent provided herein including embodiments thereof (e.g., analkylamine or a compound of formula (I), (II), or (III)) may be presentat an amount from about 0.05% (w/w) to about 10% (w/w). Thus, in someembodiments, the co-solvent (e.g., an alkylamine or a compound offormula (I), (II), or (III)) is present from about 0.05% w/w to about10% w/w. In some embodiments, the co-solvent is present from about 0.1%w/w to about 10% w/w. In other embodiments, the co-solvent is presentfrom about 0.5% w/w to about 10% w/w. In some embodiments, theco-solvent is present from about 1% w/w to about 10% w/w. In otherembodiments, the co-solvent is present from about 1.5% w/w to about 10%w/w. In some embodiments, the co-solvent is present from about 2% w/w toabout 10% w/w. In other embodiments, the co-solvent is present fromabout 2.5% w/w to about 10% w/w. In some embodiments, the co-solvent ispresent from about 3% w/w to about 10% w/w. In other embodiments, theco-solvent is present from about 3.5% w/w to about 10% w/w. In someembodiments, the co-solvent is present from about 4% w/w to about 10%w/w. In other embodiments, the co-solvent is present from about 4.5% w/wto about 10% w/w. In some embodiments, the co-solvent is present fromabout 5% w/w to about 10% w/w. In other embodiments, the co-solvent ispresent from about 5.5% w/w to about 10% w/w. In some embodiments, theco-solvent is present from about 6% w/w to about 10% w/w. In otherembodiments, the co-solvent is present from about 6.5% w/w to about 10%w/w. In some embodiments, the co-solvent is present from about 7% w/w toabout 10% w/w. In other embodiments, the co-solvent is present fromabout 7.5% w/w to about 10% w/w. In some embodiments, the co-solvent ispresent from about 8% w/w to about 10% w/w. In other embodiments, theco-solvent is present from about 8.5% w/w to about 10% w/w. In someembodiments, the co-solvent is present from about 9% w/w to about 10%w/w. In other embodiments, the co-solvent is present from about 9.5% w/wto about 10% w/w. In some embodiments, the co-solvent is present atabout 2% w/w. In other embodiments, the co-solvent is present at about0.5% w/w. A person of ordinary skill in the art will immediatelyrecognize that the above referenced values refer to weight percent ofco-solvent per volume of emulsion (i.e. total volume of aqueous andnon-aqueous solution).

The total co-solvent concentration (i.e. the total amount of allco-solvent types within the heavy crude oil emulsion compositionsprovided herein) may be from about 0.05% (w/w) to about 10% (w/w). Thus,in some embodiments, the total co-solvent concentration (i.e. the totalamount of all co-solvent types within the heavy crude oil emulsioncompositions provided herein) is from about 0.05% w/w to about 10% w/w.In some embodiments, the total co-solvent concentration is from about0.1% w/w to about 10% w/w. In other embodiments, the total co-solventconcentration is from about 0.5% w/w to about 10% w/w. In someembodiments, the total co-solvent concentration is from about 1% w/w toabout 10% w/w. In other embodiments, the total co-solvent concentrationis from about 1.5% w/w to about 10% w/w. In some embodiments, the totalco-solvent concentration is from about 2% w/w to about 10% w/w. In otherembodiments, the total co-solvent concentration is from about 2.5% w/wto about 10% w/w. In some embodiments, the total co-solventconcentration is from about 3% w/w to about 10% w/w. In otherembodiments, the total co-solvent concentration is from about 3.5% w/wto about 10% w/w. In some embodiments, the total co-solventconcentration is from about 4% w/w to about 10% w/w. In otherembodiments, the total co-solvent concentration is from about 4.5% w/wto about 10% w/w. In some embodiments, the total co-solventconcentration is from about 5% w/w to about 10% w/w. In otherembodiments, the total co-solvent concentration is from about 5.5% w/wto about 10% w/w. In some embodiments, the total co-solventconcentration is from about 6% w/w to about 10% w/w. In otherembodiments, the total co-solvent concentration is from about 6.5% w/wto about 10% w/w. In some embodiments, the total co-solventconcentration is from about 7% w/w to about 10% w/w. In otherembodiments, the total co-solvent concentration is from about 7.5% w/wto about 10% w/w. In some embodiments, the total co-solventconcentration is from about 8% w/w to about 10% w/w. In otherembodiments, the total co-solvent concentration is from about 8.5% w/wto about 10% w/w. In some embodiments, the total co-solventconcentration is from about 9% w/w to about 10% w/w. In otherembodiments, the total co-solvent concentration is from about 9.5% w/wto about 10% w/w.

In some embodiments, the emulsion composition further includes asurfactant. Where the emulsion further includes a surfactant, theemulsion may include a surfactant or a surfactant blend (e.g. aplurality of surfactant types). The surfactant provided herein may beany appropriate surfactant useful in the field of enhanced oil recoveryor transport of heavy crude oil. In some embodiments, the surfactant isa single surfactant type in the emulsion. In other embodiments, thesurfactant is a surfactant blend. A “surfactant blend” as providedherein is a mixture of a plurality of surfactant types. In someembodiments, the surfactant blend includes a first surfactant type, asecond surfactant type or a third surfactant type. The first, second andthird surfactant type may be independently different (e.g. anionic orcationic surfactants; or two anionic surfactants having a differenthydrocarbon chain length but are otherwise the same). Therefore, aperson having ordinary skill in the art will immediately recognize thatthe terms “surfactant” and “surfactant type(s)” have the same meaningand can be used interchangeably. In some embodiments, the surfactant isan anionic surfactant, a non-ionic surfactant, a zwitterionic surfactantor a cationic surfactant. In some embodiments, the surfactant is ananionic surfactant, a non-ionic surfactant, or a cationic surfactant. Inother embodiments, the surfactant is a zwitterionic surfactant.“Zwitterionic” or “zwitterion” as used herein refers to a neutralmolecule with a positive (or cationic) and a negative (or anionic)electrical charge at different locations within the same molecule.Examples for zwitterionics are without limitation betains and sultains.

The surfactant provided herein may be any appropriate anionicsurfactant. In some embodiments, the surfactant is an anionicsurfactant. In embodiments, the anionic surfactant is sodiumdodecylbenzenesulfonate (DDBSA). Sodium dodecylbenzenesulfonate (DDBSA)refers to, in the customary sense, CAS Registry No 25155-30-0. Thereterms “DDBSA” and “T-Soft” are herein used interchangeably having thesame customary meaning known in the art.

In some embodiments, the anionic surfactant is an anionic surfactantblend. Where the anionic surfactant is an anionic surfactant blend theemulsion includes a plurality (i.e. more than one) of anionic surfactanttypes. In some embodiments, the anionic surfactant is an alkoxycarboxylate surfactant, an alkoxy sulfate surfactant, an alkoxysulfonate surfactant, an alkyl sulfonate surfactant, an aryl sulfonatesurfactant or an olefin sulfonate surfactant. An “alkoxy carboxylatesurfactant” as provided herein is a compound having an alkyl or arylattached to one or more alkoxylene groups (typically —CH₂—CH(ethyl)-O—,—CH₂—CH(methyl)-O—, or —CH₂—CH₂—O—) which, in turn is attached to —COO⁻or acid or salt thereof including metal cations such as sodium. In someembodiments, the alkoxy carboxylate surfactant has the formula:

In formula (VI) or (VII) R¹ is substituted or unsubstituted C₈-C₁₅₀alkyl or substituted or unsubstituted aryl, R² is independently hydrogenor unsubstituted C₁-C₆ alkyl, R³ is independently hydrogen orunsubstituted C₁-C₆ alkyl, n is an integer from 2 to 210, z is aninteger from 1 to 6 and M⁺ is a monovalent, divalent or trivalentcation. In some embodiments, R¹ is unsubstituted linear or branchedC₈-C₃₆ alkyl. In some embodiments, R¹ is (C₆H₅—CH₂CH₂)₃C₆H₂— (TSP),(C₆H₅—CH₂CH₂)₂C₆H₃— (DSP), (C₆H₅—CH₂CH₂)₁C₆H₄— (MSP), or substituted orunsubstituted naphthyl. In some embodiments, the alkoxy carboxylate isC₂₈-25PO-25EO-carboxylate (i.e. unsubstituted C₂₈ alkyl attached to 25—CH₂—CH(methyl)-O-linkers, attached in turn to 25 —CH₂—CH₂—O— linkers,attached in turn to —COO⁻ or acid or salt thereof including metalcations such as sodium).

In some embodiments, the surfactant is an alkoxy sulfate surfactant. Analkoxy sulfate surfactant as provided herein is a surfactant having analkyl or aryl attached to one or more alkoxylene groups (typically—CH₂—CH(ethyl)-O—, —CH₂—CH(methyl)-O—, or —CH₂—CH₂—O—) which, in turn isattached to —SO₃ ⁻ or acid or salt thereof including metal cations suchas sodium. In some embodiment, the alkoxy sulfate surfactant has theformula R^(A)—(BO)_(e)—(PO)_(f)-(EO)_(g)—SO₃ ⁻ or acid or salt(including metal cations such as sodium) thereof, wherein R^(A) isC₈-C₃₀ alkyl, BO is —CH₂—CH(ethyl)-O—, PO is —CH₂—CH(methyl)-O—, and EOis —CH₂—CH₂—O—. The symbols e, f and g are integers from 0 to 25 whereinat least one is not zero. In some embodiment, the alkoxy sulfatesurfactant is C₁₅-13PO-sulfate (i.e. an unsubstituted C₁₋₅ alkylattached to 13 —CH₂—CH(methyl)-O— linkers, in turn attached to —SO₃ ⁻ oracid or salt thereof including metal cations such as sodium).

In other embodiments, the alkoxy sulfate surfactant has the formula

In formula (VIII) R¹ and R² are independently substituted orunsubstituted C₈-C₁₅₀ alkyl or substituted or unsubstituted aryl. R³ isindependently hydrogen or unsubstituted C₁-C₆ alkyl. z is an integerfrom 2 to 210. X⁻ is

and M⁺ is a monovalent, divalent or trivalent cation. In someembodiments, R¹ is branched unsubstituted C₈-C₁₅₀. In other embodiments,R¹ is branched or linear unsubstituted C₁₂-C₁₀₀ alkyl,(C₆H₅—CH₂CH₂)₃C₆H₂— (TSP), (C₆H₅—CH₂CH₂)₂C₆H₃— (DSP),(C₆H₅—CH₂CH₂)₁C₆H₄— (MSP), or substituted or unsubstituted naphthyl. Insome embodiments, the alkoxy sulfate isC₁₆-C₁₆-epoxide-15PO-10EO-sulfate (i.e. a linear unsubstituted C₁₆ alkylattached to an oxygen, which in turn is attached to a branchedunsubstituted C₁₆ alkyl, which in turn is attached to 15—CH₂—CH(methyl)-O— linkers, in turn attached to 10 —CH₂—CH₂—O— linkers,in turn attached to —SO₃ ⁻ or acid or salt thereof including metalcations such as sodium.

The alkoxy sulfate surfactant provided herein may be an aryl alkoxysulfate surfactant. An aryl alkoxy surfactant as provided herein is analkoxy surfactant having an aryl attached to one or more alkoxylenegroups (typically —CH₂—CH(ethyl)-O—, —CH₂—CH(methyl)-O—, or —CH₂—CH₂—O—)which, in turn is attached to —SO₃ ⁻ or acid or salt thereof includingmetal cations such as sodium. In some embodiments, the aryl alkoxysulfate surfactant is (C₆H₅—CH₂CH₂)₃C₆H₂-7PO-10EO-sulfate (i.e.tri-styrylphenol attached to 7 —CH₂—CH(methyl)-O— linkers, in turnattached to 10 —CH₂—CH₂—O— linkers, in turn attached to —SO₃ ⁻ or acidor salt thereof including metal cations such as sodium).

In some embodiments, the surfactant is an unsubstituted alkyl sulfate oran unsubstituted alkyl sulfonate surfactant. An alkyl sulfate surfactantas provided herein is a surfactant having an alkyl group attached to—O—SO₃ ⁻ or acid or salt thereof including metal cations such as sodium.An alkyl sulfonate surfactant as provided herein is a surfactant havingan alkyl group attached to —SO₃ ⁻ or acid or salt thereof includingmetal cations such as sodium. In some embodiments, the surfactant is anunsubstituted aryl sulfate surfactant or an unsubstituted aryl sulfonatesurfactant. An aryl sulfate surfactant as provided herein is asurfactant having an aryl group attached to —O—SO₃ ⁻ or acid or saltthereof including metal cations such as sodium. An aryl sulfonatesurfactant as provided herein is a surfactant having an aryl groupattached to —SO₃ ⁻ or acid or salt thereof including metal cations suchas sodium. In some embodiments, the surfactant is an alkyl arylsulfonate. Non-limiting examples of alkyl sulfate surfactants, arylsulfate surfactants, alkyl sulfonate surfactants, aryl sulfonatesurfactants and alkyl aryl sulfonate surfactants useful in theembodiments provided herein are alkyl aryl sulfonates (ARS) (e.g. alkylbenzene sulfonate (ABS)), alkane sulfonates, petroleum sulfonates, andalkyl diphenyl oxide (di)sulfonates. Additional surfactants useful inthe embodiments provided herein are alcohol sulfates, alcoholphosphates, alkoxy phosphate, sulfosuccinate esters, alcoholethoxylates, alkyl phenol ethoxylates, quaternary ammonium salts,betains and sultains.

The surfactant as provided herein may be an olefin sulfonate surfactant.In some embodiments, the olefin sulfonate surfactant is an internalolefin sulfonate (IOS) or an alfa olefin sulfonate (AOS). In someembodiments, the olefin sulfonate surfactant is a C₁₀-C₃₀ (IOS). In somefurther embodiments, the olefin sulfonate surfactant is C₁₅-C₁₈ IOS. Inother embodiments, the olefin sulfonate surfactant is C₁₉-C₂₈ IOS. Wherethe olefin sulfonate surfactant is C₁₅-C₁₈ IOS, the olefin sulfonatesurfactant is a mixture (combination) of C₁₅, C₁₆, C₁₇ and C₁₈ alkene,wherein each alkene is attached to a —SO₃ ⁻ or acid or salt thereofincluding metal cations such as sodium. Likewise, where the olefinsulfonate surfactant is C₁₉-C₂₈ IOS, the olefin sulfonate surfactant isa mixture (combination) of C₁₉, C₂₀, C₂₁ C₂₂, C₂₃, C₂₄, C₂₅, C₂₆, C₂₇and C₂₈ alkene, wherein each alkene is attached to a —SO₃ ⁻ or acid orsalt thereof including metal cations such as sodium. As mentioned above,the emulsion provided herein may include a plurality of surfactants(i.e. a surfactant blend). In some embodiments, the surfactant blendincludes a first olefin sulfonate surfactant and a second olefinsulfonate surfactant. In some further embodiments, the first olefinsulfonate surfactant is C₁₅-C₁₈ IOS and the second olefin sulfonatesurfactant is C₁₉-C₂₈ IOS.

Useful surfactants are disclosed, for example, in U.S. Pat. Nos.3,811,504, 3,811,505, 3,811,507, 3,890,239, 4,463,806, 6,022,843,6,225,267, 7,629,299; WIPO Patent Application WO/2008/079855,WO/2012/027757 and WO /2011/094442; as well as U.S. Patent ApplicationNos. 2005/0199395, 2006/0185845, 2006/018486, 2009/0270281,2011/0046024, 2011/0100402, 2011/0190175, 2007/0191633, 2010/004843.2011/0201531, 2011/0190174, 2011/0071057, 2011/0059873, 2011/0059872,2011/0048721, 2010/0319920, and 2010/0292110. Additional usefulsurfactants are surfactants known to be used in enhanced oil recoverymethods, including those discussed in D. B. Levitt, A. C. Jackson, L.Britton and G. A. Pope, “Identification and Evaluation ofHigh-Performance EOR Surfactants,” SPE 100089, conference contributionfor the SPE Symposium on Improved Oil Recovery Annual Meeting, Tulsa,Okla., Apr. 24-26, 2006.

A person having ordinary skill in the art will immediately recognizethat many surfactants are commercially available as blends of relatedmolecules (e.g. IOS and ABS surfactants). Thus, where a surfactant ispresent within a composition provided herein, a person of ordinary skillwould understand that the surfactant may be a blend of a plurality ofrelated surfactant molecules (as described herein and as generally knownin the art).

In some embodiment, the total surfactant concentration (i.e. the totalamount of all surfactant types within the emulsions and emulsioncompositions provided herein) in is from about 0.05% w/w to about 10%w/w. In other embodiments, the total surfactant concentration in theemulsion is from about 0.25% w/w to about 10% w/w. In other embodiments,the total surfactant concentration in the emulsion is about 0.5% w/w. Inother embodiments, the total surfactant concentration in the emulsion isabout 1.0% w/w. In other embodiments, the total surfactant concentrationin the emulsion is about 1.25% w/w. In other embodiments, the totalsurfactant concentration in the emulsion is about 1.5% w/w. In otherembodiments, the total surfactant concentration in the emulsion is about1.75% w/w. In other embodiments, the total surfactant concentration inthe emulsion is about 2.0% w/w. In other embodiments, the totalsurfactant concentration in the emulsion is about 2.5% w/w. In otherembodiments, the total surfactant concentration in the emulsion is about3.0% w/w. In other embodiments, the total surfactant concentration inthe emulsion is about 3.5% w/w. In other embodiments, the totalsurfactant concentration in the emulsion is about 4.0% w/w. In otherembodiments, the total surfactant concentration in the emulsion is about4.5% w/w. In other embodiments, the total surfactant concentration inthe emulsion is about 5.0% w/w. In other embodiments, the totalsurfactant concentration in the emulsion is about 5.5% w/w. In otherembodiments, the total surfactant concentration in the emulsion is about6.0% w/w. In other embodiments, the total surfactant concentration inthe emulsion is about 6.5% w/w. In other embodiments, the totalsurfactant concentration in the emulsion is about 7.0% w/w. In otherembodiments, the total surfactant concentration in the emulsion is about7.5% w/w. In other embodiments, the total surfactant concentration inthe emulsion is about 8.0% w/w. In other embodiments, the totalsurfactant concentration in the emulsion is about 9.0% w/w. In otherembodiments, the total surfactant concentration in the emulsion is about10% w/w.

In some embodiments, the emulsion composition further includes an alkaliagent. An alkali agent as provided herein is a basic, ionic salt of analkali metal (e.g. lithium, sodium, potassium) or alkaline earth metalelement (e.g. magnesium, calcium, barium, radium). In some embodiments,the alkali agent is NaOH, KOH, LiOH, Na₂CO₃, NaHCO₃, Na-metaborate, Nasilicate, Na orthosilicate, or NH₄OH. The emulsion composition mayinclude seawater, or fresh water from an aquifer, river or lake. In someembodiments, the emulsion composition includes hard brine or soft brine.In some further embodiments, the water is soft brine. In some furtherembodiments, the water is hard brine. Where the emulsion compositionincludes soft brine, the aqueous composition may include an alkaliagent. In soft brine the alkali agent provides for enhanced soapgeneration from the oils, lower surfactant adsorption to the solidmaterial (e.g. rock) in the reservoir and increased solubility ofviscosity enhancing water soluble polymers. In some embodiment, thealkali agent is present in the emulsion composition at a concentrationfrom about 0.1% w/w to about 3% w/w.

The heavy crude oil emulsion compositions provided herein may furtherinclude a salt to increase the salinity of the emulsion composition.Thus, in some embodiments, the heavy crude oil composition furtherincludes a salt. In some embodiments, the salt is NaCl, Na₂SO₄, K₂SO₄ orKCl. In some embodiments, the salt is NaCl or KCl. The salt included inthe heavy crude oil emulsion compositions provided herein may be presentin an amount sufficient to increase the activity of the in situgenerated soap, which is formed through the reaction of the carboxylicacids in the oil with the alkali agent and/or basic co-solvent. Theactivity of the in situ generated soap refers to the surface activity ofthe in situ generated soap. In some embodiments, the salt is present inan amount sufficient to decrease the interfacial tension between thewater and the heavy crude oil. In some embodiments, the salt is presentin an amount sufficient to decrease the interfacial viscosity of theemulsion. In some embodiments, the salt is present in an amountsufficient to increase the solubility of the co-solvent or alkali agentin the emulsion relative to the absence of the salt. In other words, inthe presence of a sufficient amount of the salt, the solubility of theco-solvent or the alkali agent in the heavy crude oil emulsioncomposition is higher than in the absence of the salt.

The salt may be present in the heavy crude oil emulsion composition fromabout 0.01% to about 2% (w/v). Thus in some embodiments, the salt ispresent from about 0.01% to about 2% (w/v). In other embodiments, thesalt is present from about 0.05% to about 2% (w/v). In otherembodiments, the salt is present from about 0.1% to about 2% (w/v). Inother embodiments, the salt is present from about 0.2% to about 2%(w/v). In other embodiments, the salt is present from about 0.3% toabout 2% (w/v). In other embodiments, the salt is present from about0.4% to about 2% (w/v). In other embodiments, the salt is present fromabout 0.5% to about 2% (w/v). In other embodiments, the salt is presentfrom about 0.6% to about 2% (w/v). In other embodiments, the salt ispresent from about 0.7% to about 2% (w/v). In other embodiments, thesalt is present from about 0.8% to about 2% (w/v). In other embodiments,the salt is present from about 0.9% to about 2% (w/v). In otherembodiments, the salt is present from about 1.0% to about 2% (w/v). Inother embodiments, the salt is present from about 1.2% to about 2%(w/v). In other embodiments, the salt is present from about 1.4% toabout 2% (w/v). In other embodiments, the salt is present from about1.6% to about 2% (w/v). In other embodiments, the salt is present fromabout 1.8% to about 2% (w/v).

In some embodiments, the salt is present from about 0.01% to about 1%(w/v). In other embodiments, the salt is present from about 0.05% toabout 1% (w/v). In other embodiments, the salt is present from about0.1% to about 1% (w/v). In other embodiments, the salt is present fromabout 0.2% to about 1% (w/v). In other embodiments, the salt is presentfrom about 0.3% to about 1% (w/v). In other embodiments, the salt ispresent from about 0.4% to about 1% (w/v). In other embodiments, thesalt is present from about 0.5% to about 1% (w/v). In other embodiments,the salt is present from about 0.6% to about 1% (w/v). In otherembodiments, the salt is present from about 0.7% to about 1% (w/v). Inother embodiments, the salt is present from about 0.8% to about 1%(w/v). In other embodiments, the salt is present from about 0.9% toabout 1% (w/v). In one embodiment, the salt is present at an amount ofabout 0.1% (w/v). In another embodiment, the salt is present at anamount of about 0.8% (w/v). A person of ordinary skill in the art willimmediately recognize that the above referenced values refer to weightpercent of salt per volume of aqueous solution.

The heavy crude oil emulsion compositions provided herein may furtherinclude seawater, or fresh water from an aquifer, river or lake. In someembodiments, the water is hard brine. In other embodiments, the water issoft brine. In some embodiments, the brine is derived from the samereservoir as the heavy crude oil. In other embodiments, the brine isderived from a different reservoir than the heavy crude oil. In someembodiments, salt is removed from the brine.

In other embodiments, the emulsion further includes a catalyst. Thecatalyst provided herein may be any appropriate catalyst useful in thefield of enhanced oil recovery or transport of heavy crude oil. In someembodiments, the catalyst is a single catalyst type in the emulsion. Inother embodiments, the catalyst is a catalyst blend. A “catalyst blend”as provided herein is a mixture of a plurality of catalyst types. Insome embodiments, the catalyst blend includes a first catalyst type, asecond catalyst type or a third catalyst type. The first, second andthird catalyst type may be independently different (e.g. anionic orcationic catalysts; or two cationic catalyst having a differenthydrocarbon chain length but are otherwise the same). Therefore, aperson having ordinary skill in the art will immediately recognize thatthe terms “catalyst” and “catalyst type(s)” have the same meaning andcan be used interchangeably. In some embodiments, the catalyst is ananoparticle. In other embodiments, the catalyst is platinum, palladium,rhodium, or nickel. In some embodiments, the catalyst is chromium oxide,Pt/Al₂O₃, or zinc titanium oxide. In other embodiments, the catalyst isaluminum oxide or zeolites.

In some embodiments, the emulsion is at a transport temperature. Atransport temperature as provided herein refers to a temperature atwhich a heavy crude oil emulsion is transported in a transport vessel(e.g. an oil pipeline). A “transport vessel” as used herein, refers to acontainer used for transporting oil, typically large amounts of oil(e.g. at least hundreds of gallons, at least thousands of gallons, atleast millions of gallons or at least billions of gallons). A transportvessel includes a storage vessel contained within a petroleum tanker(oil tankers), barge, truck or a train. A transport vessel also includesan petroleum pipeline (oil pipeline). The transport temperature of aheavy crude oil emulsion may be less than the temperature of the heavycrude oil in the reservoir or less than the temperature of the heavycrude oil after extraction from the reservoir. In some embodiments, thetransport temperature is less than 100° C. In some embodiments, thetransport temperature is less than 70° C. In some embodiments, thetransport temperature is less than 60° C. In other embodiments, thetransport temperature is less than 55° C. In some embodiments, thetransport temperature is less than 50° C. In other embodiments, thetransport temperature is less than 45° C. In some embodiments, thetransport temperature is less than 40° C. In other embodiments, thetransport temperature is less than 35° C. In some embodiments, thetransport temperature is less than 30° C. In other embodiments, thetransport temperature is less than 25° C. In some embodiments, thetransport temperature is less than 20° C. In other embodiments, thetransport temperature is less than 15° C.

In some embodiments, the transport temperature is from about 0° C. toabout 70° C. In some embodiments, the transport temperature is fromabout 10° C. to about 70° C. In some embodiments, the transporttemperature is from about 15° C. to about 70° C. In other embodiments,the transport temperature is from about 20° C. to about 70° C. In otherembodiments, the transport temperature is from about 25° C. to about 70°C. In other embodiments, the transport temperature is from about 30° C.to about 70° C. In other embodiments, the transport temperature is fromabout 35° C. to about 70° C. In other embodiments, the transporttemperature is from about 40° C. to about 70° C. In other embodiments,the transport temperature is from about 45° C. to about 70° C. In otherembodiments, the transport temperature is from about 50° C. to about 70°C. In other embodiments, the transport temperature is from about 55° C.to about 70° C. In some embodiments, the transport temperature is fromabout 0° C. to about 60° C. In other embodiments, the transporttemperature is from about 5° C. to about 60° C. In some embodiments, thetransport temperature is from about 10° C. to about 60° C. In someembodiments, the transport temperature is from about 15° C. to about 60°C. In other embodiments, the transport temperature is from about 20° C.to about 60° C. In other embodiments, the transport temperature is fromabout 25° C. to about 60° C. In other embodiments, the transporttemperature is from about 30° C. to about 60° C. In other embodiments,the transport temperature is from about 35° C. to about 60° C. In otherembodiments, the transport temperature is from about 40° C. to about 60°C. In other embodiments, the transport temperature is from about 45° C.to about 60° C. In other embodiments, the transport temperature is fromabout 50° C. to about 60° C. In other embodiments, the transporttemperature is from about 55° C. to about 60° C. In some embodiments,the transport temperature is about 0° C., 5° C., 10° C., 15° C., 20° C.,25° C., 30° C., 35° C., 40° C., 45° C., 50° C., 55° C., 60° C., 65° C.or 70° C. In some embodiments, the transport temperature is an ambienttemperature. An ambient temperature as provided herein may be atemperature of less than 80° C. Thus, in embodiments, the ambienttemperature is less than 80° C. In embodiments, the ambient temperatureis less than 60° C. In embodiments, the ambient temperature is less than40° C. In embodiments, the ambient temperature is 20° C.

The heavy crude oil emulsion compositions provided herein include abroad concentration of heavy crude oil. In some embodiments, the heavycrude oil is present from about 10% to about 95% (v/v). In otherembodiments, the heavy crude oil is present from about 15% to about 95%(v/v), from about 20% to about 95% (v/v), from about 25% to about 95%(v/v), from about 30% to about 95% (v/v), from about 35% to about 95%(v/v), from about 40% to about 95% (v/v), from about 45% to about 95%(v/v), from about 50% to about 95% (v/v), from about 55% to about 95%(v/v), from about 60% to about 95% (v/v), from about 65% to about 95%(v/v), from about 70% to about 95% (v/v), from about 75% to about 95%(v/v), from about 80% to about 95% (v/v), from about 85% to about 95%(v/v) or from about 90% to about 95% (v/v). In some embodiments, theheavy crude oil is present at about 10%, 15%, 20%, 25%, 30%, 35%, 40%,45%, 50%, 55%, 60%, 65%, 70%, 75%, 80%, 85%, 90% or 95% (v/v). In someembodiments, the heavy crude oil is present at about 20% (v/v). In otherembodiments, the heavy crude oil is present at about 40% (v/v). In otherembodiments, the heavy crude oil is present at about 60% (v/v). In otherembodiments, the heavy crude oil is present at about 80% (v/v). A personof ordinary skill in the art will immediately recognize that the abovereferenced values refer to volume percent per volume of emulsion.

As described above, the heavy crude oils included in the emulsioncompositions provided herein are highly viscous. In some embodiments,the viscosity of the heavy crude oil is about 100,000 cP. In otherembodiments, the viscosity of the heavy crude oil is about 200,000 cP.In some embodiments, the viscosity of the heavy crude oil is about300,000 cP. In some embodiments, the viscosity of the heavy crude oil isabout 1,000,000 cP. In some embodiments, the viscosity of the heavycrude oil is about 100,000 cP at ambient temperature. In otherembodiments, the viscosity of the heavy crude oil is about 200,000 cP atambient temperature. In some embodiments, the viscosity of the heavycrude oil is about 300,000 cP at ambient temperature. In someembodiments, the viscosity of the heavy crude oil is about 1,000,000 cPat ambient temperature.

Upon formation of a heavy crude oil emulsion according to thecompositions and methods provided herein, the viscosity of the heavycrude oil emulsion decreases and remains low over extended periods oftime and at ambient temperatures. In some embodiments, the viscosity ofthe emulsion is lower than the viscosity of the heavy crude oil. In someembodiments, the viscosity of the emulsion is about a 10 times less thanthe viscosity of the heavy crude oil. In some embodiments, the viscosityof the emulsion is about a 100 times less than the viscosity of theheavy crude oil. In some embodiments, the viscosity of the emulsion isabout a 1,000 times less than the viscosity of the heavy crude oil. Inother embodiments, the viscosity of the emulsion is about a 10,000 timesless than the viscosity of the heavy crude oil. In other embodiments,the viscosity of the emulsion is about a 100,000 times less than theviscosity of the heavy crude oil. The formation of low viscosity heavycrude oil emulsions according to the compositions and methods providedherein allows for cost effective and efficient transport of a heavycrude oil. Thus, the emulsion compositions provided herein may be withina vessel. In some embodiments, the emulsion is within a vessel. In afurther embodiment, the vessel is a pipeline. In another furtherembodiment, the vessel forms part of transportation vehicle. Atransportation vehicle as provided herein refers to a vehicleappropriate for the transport of heavy crude oil emulsions. Examples oftransportation vehicles are without limitation vehicles appropriate forground transportation (e.g. trucks, trains), water transportation (e.g.sea or river) and air transportation. In some embodiments, the emulsionis transported in a pipeline.

The heavy crude oil emulsion compositions as provided herein aresurprisingly stable at ambient temperature. A heavy crude oil emulsioncomposition is stable, when it retains the same features (e.g.viscosity) over an extended period of time (e.g. hours, days, weeks,months). As described above, the heavy crude oil emulsions providedherein have a viscosity that is at least 1,000-fold lower than theviscosity of the heavy crude oil. Surprisingly, the heavy crude oilemulsion compositions provided herein maintain a low viscosity, which isat least 1,000-fold lower than the viscosity of the heavy crude oil, atambient temperature and for extended periods of time. An ambienttemperature as provided herein may be a temperature of less than 80° C.Thus, in some embodiments, the ambient temperature is less than 80° C.In other embodiments, the ambient temperature is less than 60° C. Insome embodiments, the ambient temperature is less than 40° C. In someembodiments, the emulsion is stable at ambient temperature for at leastan hour. In some embodiments, the emulsion is stable at ambienttemperature for at least a day. In some embodiments, the emulsion isstable at ambient temperature for at least a week. In some embodiments,the heavy crude oil emulsion is stable at the transport temperature forat least an hour. In some embodiments, the heavy crude oil emulsion isstable at the transport temperature for at least a day. In someembodiments, the heavy crude oil emulsion is stable at the transporttemperature for at least a week. In other embodiments, the heavy crudeoil emulsion is stable at the transport temperature for at least amonth.

In one embodiment, the heavy crude oil emulsion includes a heavy crudeoil at 40% (v/v); a co-solvent wherein the co-solvent istriethylenetetramine (TETA), present at 2% w/w; and a salt, wherein thesalt is NaCl present 0.1% (w/v). In another embodiment, the heavy crudeoil emulsion includes a heavy crude oil at 40% (v/v); a co-solventwherein the co-solvent is dimethylaminopropylamine (DMAPA), present at2% w/w; and a salt, wherein the salt is NaCl present 0.1% (w/v). In oneembodiment, the heavy crude oil emulsion includes a heavy crude oil at40% (w/v); a co-solvent wherein the co-solvent is triethylenetetramine(TETA), present at 1% w/w; and a salt, wherein the salt is NaCl present0.1% (w/v).

In one aspect, a heavy crude oil emulsion is provided. The heavy crudeoil emulsion includes a heavy crude oil, water and an alkylamine and theheavy crude oil emulsion is within a transport vessel. The alkylaminemay be an alkylamine as described herein including embodiments thereof(e.g. an alkylpolyamine). Thus, in some embodiments, the alkylamine istriethylenetetramine. In other embodiments, the alkylamine isdimethylaminopropylamine. In one embodiment, the emulsion does notinclude a compound of formula (I), (II), or (III). In anotherembodiment, the emulsion does not include a surfactant. In oneembodiment, the emulsion does not include an alkali agent.

As described above the emulsion composition provided herein includes aheavy crude oil, water, a salt and a co-solvent, wherein the co-solventis an alkylamine or a compound having the formula (I). In oneembodiment, the heavy crude oil is present at about 85%, the co-solventis DIPA-15EO present at about 1.5% (w/v), 2.5% (w/v), 3% (w/v), or 3.5%(w/v), and the salt is NaCl, present at about 0.2% (w/v). In oneembodiment, the heavy crude oil is present at about 85% (w/v), theco-solvent is DIPA-15EO present at about 1.5% (w/v) and the salt isNaCl, present at about 0.4% (w/v). In one embodiment, the heavy crudeoil is present at about 85% (w/v), the co-solvent is DIPA-15EO presentat about 2.5% (w/v) and the salt is NaCl, present at about 0.5% (w/v).In one embodiment, the heavy crude oil is present at about 80% (w/v),85% (w/v) or 90% (w/v), the co-solvent is DIPA-15EO present at about1.5% (w/v) and the salt is NaCl, present at about 0.2% (w/v). In oneembodiment, the heavy crude oil is present at about 20% (w/v), 40%(w/v), 60% (w/v), 80% (w/v) or 100% (w/v), the co-solvent is DIPA-15EOpresent at about 1.5% (w/v) and the salt is NaCl, present at about 1%(w/v). A person of ordinary skill in the art will immediately recognizethat the above referenced values for the concentration of co-solventrefer to weight percent per volume of water and oil combined. The abovereferenced values for the concentration of other components (e.g., salt)refer to weight percent per volume of aqueous solution.

In one embodiment, the heavy crude oil is present at about 40% (w/v),the co-solvent is DMAPA present at about 2% (w/v) and the salt is NaCl,present at about 0.1% (w/v). In one embodiment, the heavy crude oil ispresent at about 40% (w/v), the co-solvent is DIPA-15EO present at about2% (w/v) and the salt is NaCl, present at about 0.1% (w/v). In oneembodiment, the heavy crude oil is present at about 40% (w/v), theco-solvent is TETA present at about 2% (w/v) and the salt is NaCl,present at about 0.1% (w/v). In one embodiment, the heavy crude oil ispresent at about 60% (w/v), the co-solvent is DIPA-15EO present at about3% (w/v) and the salt is NaCl, present at about 0.1% (w/v). A person ofordinary skill in the art will immediately recognize that the abovereferenced values for the concentration of co-solvent refer to weightpercent per volume of water and oil combined. The above referencedvalues for the concentration of other components (e.g., salt) refer toweight percent per volume of aqueous solution.

As described above the heavy crude oil emulsion provided herein includesan co-solvent, wherein the co-solvent and the additional co-solvent forma co-solvent blend. In one embodiment, the heavy crude oil is present atabout 20% (w/v), 60% (w/v) or 80% (w/v), the co-solvent is DIPA-15EO,present at about 1.5% (w/v), the additional co-solvent is a compound offormula (VA), wherein R¹ and R² are hydrogen and n is 10, present at0.5% (w/v) and the salt is NaCl, present at about 1% (w/v). A person ofordinary skill in the art will immediately recognize that the abovereferenced values for the concentration of co-solvent or additionalco-solvent refer to weight percent per volume of water and oil combined.The above referenced values for the concentration of other components(e.g., salt) refer to weight percent per volume of aqueous solution.

The heavy crude oil emulsion provided herein may further include asurfactant. In one embodiment, the heavy crude oil is present at about85% (w/v), the co-solvent is DIPA-15EO, present at about 1.5% (w/v), thesurfactant is DDBSA, present at 0.5% (w/v) and the salt is NaCl, presentat about 0.2% (w/v). A person of ordinary skill in the art willimmediately recognize that the above referenced values for theconcentration of co-solvent refer to weight percent per volume of waterand oil combined. The above referenced values for the concentration ofother components (e.g., surfactant, salt) refer to weight percent pervolume of aqueous solution.

In another aspect, a heavy crude oil emulsion is provided. The heavycrude oil emulsion includes a first phase and a second phase, whereinthe first phase includes an oil-immiscible compound and the second phaseincludes a heavy crude oil.

In one aspect, a heavy crude oil emulsion is provided. The heavy crudeoil emulsion includes an amphiphilic co-solvent, a first phase and asecond phase, wherein the first phase includes an oil-immisciblecompound and the second phase includes a heavy crude oil. Theamphiphilic co-solvent is an alkylamine or a compound having theformula:

In formula (I) R^(1A) and R^(1B) are independently hydrogen,unsubstituted C₁-C₈ alkyl, unsubstituted cycloalkyl, unsubstitutedheterocycloalkyl, unsubstituted aryl, unsubstituted heteroaryl, C₁-C₆alkylamine or

R² and R³ are independently hydrogen or unsubstituted C₁-C₂ alkyl, n isan integer from 1 to 30 and m is an integer from 1 to 30.

The heavy crude oil emulsions provided herein include oil-immisciblecompounds and/or amphiphilic co-solvents. An “oil-immiscible compound”as referred to herein is a compound that is not soluble in heavy crudeoil. In one embodiment, the oil-immiscible compound is only lightlysoluble in heavy crude oil. In embodiments, the oil-immiscible compoundis a liquid. An oil-immiscible compound is capable of lubricatingviscous crude oil and has a lower viscosity than the heavy crude oil.Upon formation of the heavy crude oil emulsion the oil-immisciblecompound is within the first phase of the emulsion and is capable offacilitating the interaction of other components (e.g., co-solvent,alkali agent, surfactant) with the crude oil. Thus, in some embodiments,the oil-immiscible compound forms part of the first phase of theemulsion. In yet another embodiment, the oil-immiscible compound formspart of an interface between the first phase and the second phase of theemulsion In embodiments, the oil immiscible compound is ethylene glycol,di-ethylene glycol, glycerol, propylene glycol, pentaerythritol,sorbitol or methanol. In embodiments, the oil-immiscible compound isethylene glycol. In embodiments, the oil-immiscible compound isglycerol. In embodiments, the oil immiscible compound is ethyleneglycol, di-ethylene glycol, propylene glycol, sorbitol, ethanol,isopropanol, secondary butanol or methanol. In embodiments, theoil-immiscible compound is ethylene glycol. In embodiments, theoil-immiscible compound is methanol. In embodiments, the oil immisciblecompound is ethylene glycol, di-ethylene glycol, propylene glycol,dimethyl ether, pentaerythritol sorbitol, ethanol, isopropanol,secondary butanol or methanol. In embodiments, the oil immisciblecompound is ethylene glycol, di-ethylene glycol, propylene glycol,dimethyl ether, pentaerythritol sorbitol, ethanol, isopropanol,secondary butanol or methanol. A person of ordinary skill in the artwill immediately recognize that the above referenced values for theconcentration of co-solvent refer to weight percent per volume of waterand oil combined (i.e. emulsion). The above referenced values for theconcentration of other components (salt, alkali agent) refer to weightpercent per volume of aqueous solution.

In embodiments, the oil-immiscible compound is present at about 5%(w/v). In embodiments, the oil-immiscible compound is present at about10% (w/v). In embodiments, the oil-immiscible compound is present atabout 15% (w/v). In embodiments, the oil-immiscible compound is presentat about 20% (w/v). In embodiments, the oil-immiscible compound ispresent at about 25% (w/v). In embodiments, the oil-immiscible compoundis present at about 30% (w/v). In embodiments, the oil-immisciblecompound is present at about 35% (w/v). In embodiments, theoil-immiscible compound is present at about 40% (w/v). In embodiments,the oil-immiscible compound is present at about 45% (w/v). Inembodiments, the oil-immiscible compound is present at about 50% (w/v).In embodiments, the oil-immiscible compound is present at about 55%(w/v). In embodiments, the oil-immiscible compound is present at about60% (w/v). A person of ordinary skill in the art will immediatelyrecognize that the above referenced values for the concentration ofco-solvent refer to weight percent per volume of water and oil combined(i.e. emulsion). The above referenced values for the concentration ofother components (salt, basic agent) refer to weight percent per volumeof aqueous solution.

In embodiments, the oil-immiscible compound is present from about 5%(w/v) to about 70% (w/v). In embodiments, the oil-immiscible compound ispresent from about 10% (w/v) to about 70% (w/v). In embodiments, theoil-immiscible compound is present from about 15% (w/v) to about 70%(w/v). In embodiments, the oil-immiscible compound is present from about20% (w/v) to about 70% (w/v). In embodiments, the oil-immisciblecompound is present from about 25% (w/v) to about 70% (w/v). Inembodiments, the oil-immiscible compound is present from about 30% (w/v)to about 70% (w/v). In embodiments, the oil-immiscible compound ispresent from about 35% (w/v) to about 70% (w/v). In embodiments, theoil-immiscible compound is present from about 40% (w/v) to about 70%(w/v). In embodiments, the oil-immiscible compound is present from about45% (w/v) to about 70% (w/v). In embodiments, the oil-immisciblecompound is present from about 50% (w/v) to about 70% (w/v). Inembodiments, the oil-immiscible compound is present from about 55% (w/v)to about 70% (w/v). In embodiments, the oil-immiscible compound ispresent from about 60% (w/v) to about 70% (w/v). In embodiments, theoil-immiscible compound is present from about 65% (w/v) to about 70%(w/v).

In embodiments, the first phase is about 5% oil-immiscible compound. Inembodiments, the first phase is about 10% oil-immiscible compound. Inembodiments, the first phase is about 15% oil-immiscible compound. Inembodiments, the first phase is about 20% oil-immiscible compound. Inembodiments, the first phase is about 25% oil-immiscible compound. Inembodiments, the first phase is about 30% oil-immiscible compound. Inembodiments, the first phase is about 35% oil-immiscible compound. Inembodiments, the first phase is about 40% oil-immiscible compound. Inembodiments, the first phase is about 45% oil-immiscible compound. Inembodiments, the first phase is about 50% oil-immiscible compound. Inembodiments, the first phase is about 55% oil-immiscible compound. Inembodiments, the first phase is about 60% oil-immiscible compound. Inembodiments, the first phase is about 65% oil-immiscible compound. Inembodiments, the first phase is about 70% oil-immiscible compound. Inembodiments, the first phase is about 75% oil-immiscible compound. Inembodiments, the first phase is about 80% oil-immiscible compound. Inembodiments, the first phase is about 85% oil-immiscible compound. Inembodiments, the first phase is about 90% oil-immiscible compound. Inembodiments, the first phase is about 95% oil-immiscible compound. Inembodiments, the first phase is about 98% oil-immiscible compound. Inembodiments, the first phase is about 99% oil-immiscible compound. Aperson of ordinary skill in the art will immediately recognize that theabove referenced values refer to weight percent per volume of theemulsion.

An “amphiphilic co-solvent” refers to a co-solvent as provided herein(e.g., a compound of formula (I), (II), (III), or a co-solvent blend asdescribed herein), including embodiments thereof, which is at leastpartially soluble in both the first phase including the oil-immisciblecompound, and the second phase including the heavy crude oil. Therefore,the amphiphilic co-solvent is by definition chemically distinct from theoil-immiscible compound. In embodiments, the amphiphilic co-solventforms part of the first phase. In embodiments, the amphiphilicco-solvent forms part of the second phase. In embodiments, theamphiphilic co-solvent forms part of the first phase and the secondphase. In embodiments, the amphiphilic co-solvent is present in thefirst phase and the second phase. In embodiments, the first phaseincludes an alkali agent. Where the heavy crude oil emulsion includes anamphiphilic co-solvent any co-solvent useful in enhanced oil recoveryand transport of heavy oil may be used. Examples of co-solvents usefulfor the emulsions and methods provided herein have been described above(e.g., a compound of formula ((I), (II), (III), or a co-solvent blend asdescribed herein). An amphiphilic co-solvent as provided herein ispresent at the same concentrations described herein for co-solvents.Thus, in embodiments, the amphiphilic co-solvent is present at about0.01% (w/v) to 5% (w/v). A person of ordinary skill in the art willimmediately recognize that the above referenced values for theconcentration of amphiphilic co-solvent refer to weight percent pervolume of first and second phase (i.e., water and oil combined oremulsion).

In embodiments, the heavy crude oil emulsion includes an additionalco-solvent as described above. Thus, in embodiments, the additionalco-solvent forms part of the first and the second phase. In embodiments,the additional co-solvent has the formula

In formula (IV), L¹ is unsubstituted C₁-C₆ alkylene, unsubstitutedphenylene, unsubstituted cyclohexylene, unsubstituted cyclopentylene ormethyl-substituted cyclopentylene. R² is independently hydrogen, methylor ethyl. R³ is independently hydrogen or

R⁴ is independently hydrogen, methyl or ethyl, n is an integer i from 0to 30, and m is an integer from 0 to 30.

In some embodiments, the additional co-solvent has the formula

In formula (V) R¹ is independently hydrogen, unsubstituted C₁-C₆ alkylor R⁵—OH, R² is independently hydrogen or unsubstituted C₁-C₂ alkyl, R⁵is independently a bond or unsubstituted C₁-C₆ alkyl, n is an integerfrom 1 to 30, o is an integer from 1 to 5 and z is an integer from 1 to5.

In some embodiments, the additional co-solvent has the formula

In formula (VA) R¹ is independently hydrogen or unsubstituted C₁-C₆alkyl, R² is independently hydrogen or unsubstituted C₁-C₂ alkyl and nis an integer from 1 to 30. In embodiments, the additional co-solvent ispresent at a concentration from about 0.01% w/w to about 5% w/w.

In embodiments, the heavy crude oil emulsion does not include water. Inembodiments, the heavy crude oil emulsion does not include added water.In embodiments, the heavy crude oil emulsion does not include exogenouswater. Where the heavy crude oil emulsion does not include exogenouswater no water is added to the emulsion. In embodiments, the heavy crudeoil emulsion is anhydrous. In embodiments, the heavy crude oil emulsionincludes traces of water. Where the heavy crude oil emulsion includestraces of water, the heavy crude oil emulsion includes less than about0.01% (w/v) water. In embodiments, the heavy crude oil emulsion includesless than about 20% (w/v) water. In embodiments, the heavy crude oilemulsion includes less than about 15% (w/v) water. In embodiments, theheavy crude oil emulsion includes less than about 10% (w/v) water. Inembodiments, the heavy crude oil emulsion includes less than about 5%(w/v) water. In embodiments, the heavy crude oil emulsion includes lessthan about 4% (w/v) water. In embodiments, the heavy crude oil emulsionincludes less than about 3% (w/v) water. In embodiments, the heavy crudeoil emulsion includes less than about 2% (w/v) water. In embodiments,the heavy crude oil emulsion includes less than about 1% (w/v) water. Inembodiments, the heavy crude oil emulsion includes less than about 0.5%(w/v) water. In embodiments, the heavy crude oil emulsion includes lessthan about 0.4% (w/v) water. In embodiments, the heavy crude oilemulsion includes less than about 0.3% (w/v) water. In embodiments, theheavy crude oil emulsion includes less than about 0.2% (w/v) water. Inembodiments, the heavy crude oil emulsion includes less than about 0.1%(w/v) water. In embodiments, the heavy crude oil emulsion includes lessthan about 0.01% (w/v) water. A person of ordinary skill in the art willimmediately recognize that the above referenced values refer to weightpercent per volume of emulsion.

In embodiments, the first phase further includes heavy crude oil water.“Heavy crude oil water” is water that is endogenous to the heavy crudeoil and refers to the water found in the heavy crude oil as extracted.In embodiments, the amount of heavy crude oil water in a heavy crude oilis from about 0.01% (w/v) to about 95% w/v. In embodiments, the amountof heavy crude oil water in a heavy crude oil is from about 1% (w/v) toabout 95% w/v. In embodiments, the amount of heavy crude oil water in aheavy crude oil is from about 5% (w/v) to about 95% w/v. In embodiments,the amount of heavy crude oil water in a heavy crude oil is from about10% (w/v) to about 95% w/v. In embodiments, the amount of heavy crudeoil water in a heavy crude oil is from about 15% (w/v) to about 95% w/v.In embodiments, the amount of heavy crude oil water in a heavy crude oilis from about 20% (w/v) to about 95% w/v. In embodiments, the amount ofheavy crude oil water in a heavy crude oil is from about 30% (w/v) toabout 95% w/v. In embodiments, the amount of heavy crude oil water in aheavy crude oil is from about 40% (w/v) to about 95% w/v. Inembodiments, the amount of heavy crude oil water in a heavy crude oil isfrom about 50% (w/v) to about 95% w/v. In embodiments, the amount ofheavy crude oil water in a heavy crude oil is from about 60% (w/v) toabout 95% w/v. In embodiments, the amount of heavy crude oil water in aheavy crude oil is from about 70% (w/v) to about 95% w/v. Inembodiments, the amount of heavy crude oil water in a heavy crude oil isfrom about 80% (w/v) to about 95% w/v. In embodiments, the amount ofheavy crude oil water in a heavy crude oil is from about 90% (w/v) toabout 95% w/v.

In embodiments, the heavy crude oil water is present at about 95% (w/v).In embodiments, the heavy crude oil water is present at about 90% (w/v).In embodiments, the heavy crude oil water is present at about 85% (w/v).In embodiments, the heavy crude oil water is present at about 80% (w/v).In embodiments, the heavy crude oil water is present at about 75% (w/v).In embodiments, the heavy crude oil water is present at about 60% (w/v).In embodiments, the heavy crude oil water is present at about 65% (w/v).In embodiments, the heavy crude oil water is present at about 50% (w/v).In embodiments, the heavy crude oil water is present at about 45% (w/v).In embodiments, the heavy crude oil water is present at about 40% (w/v).In embodiments, the heavy crude oil water is present at about 35% (w/v).In embodiments, the heavy crude oil water is present at about 30% (w/v).In embodiments, the heavy crude oil water is present at about 25% (w/v).In embodiments, the heavy crude oil water is present at about 20% (w/v).In embodiments, the heavy crude oil water is present at about 15% (w/v).In embodiments, the heavy crude oil water is present at about 10% (w/v).In embodiments, the heavy crude oil water is present at about 5% (w/v).In embodiments, the heavy crude oil water is present at about 4% (w/v).In embodiments, the heavy crude oil water is present at about 3% (w/v).In embodiments, the heavy crude oil water is present at about 2% (w/v).In embodiments, the heavy crude oil water is present at about 1% (w/v).In embodiments, the heavy crude oil water is present at about 0.5%(w/v). In embodiments, the heavy crude oil water is present at about0.1% (w/v). In embodiments, the heavy crude oil water is present atabout 0.01% (w/v). In embodiments, traces of the heavy crude oil waterare present in the heavy crude oil emulsion. Where traces of the heavycrude oil water are present in the heavy crude oil emulsion, the heavycrude oil emulsion includes less than 0.01% (w/v) of heavy crude oilwater. In embodiments, the heavy crude oil emulsion does not includeheavy crude oil water. In embodiments, the amount of water in the heavycrude oil emulsion is equal to the amount of the heavy crude oil water.A person of ordinary skill in the art will immediately recognize thatthe above referenced values refer to weight percent per volume ofemulsion.

In embodiments, the heavy crude oil emulsion includes a surfactant.Where the heavy crude oil emulsion includes a surfactant any surfactantuseful in enhanced oil recovery and transport of heavy oil may be used.Examples of surfactants useful for the methods provided have beendescribed above. In embodiments, the viscosity of the emulsion is lowerthan the viscosity of the heavy crude oil. In embodiments, the emulsionis formed at an ambient temperature.

As described above the emulsion composition provided herein includes aheavy crude oil, an amphiphilic co-solvent, an oil-immiscible compoundand a heavy crude oil, wherein the amphiphilic co-solvent is analkylamine or a compound having the formula (I). In one embodiment, theheavy crude oil is present at about 80%, the co-solvent is DIPA-15EOpresent at about 0.6% (w/v), and the oil-immiscible compound is ethyleneglycol, present at about 15% (w/v). In a further embodiment, the heavycrude oil emulsion includes heavy crude oil water. In another furtherembodiment, the heavy crude oil water is present at about 4.4% (w/v).

In another aspect, a non-aqueous composition including an oil-immisciblecompound and an amphiphilic co-solvent is provided. The amphiphilicco-solvent is an alkylamine or a compound having the formula:

In formula (I) R^(1A) and R^(1B) are independently hydrogen,unsubstituted C₁-C₈ alkyl, unsubstituted cycloalkyl, unsubstitutedheterocycloalkyl, unsubstituted aryl, unsubstituted heteroaryl, C₁-C₆alkylamine or

R² and R³ are independently hydrogen or unsubstituted C₁-C₂ alkyl, n isan integer from 1 to 30 and m is an integer from 1 to 30. Inembodiments, the oil immiscible compound is ethylene glycol, di-ethyleneglycol, glycerol, propylene glycol, pentaerythritol, sorbitol ormethanol. In embodiments, the oil-immiscible compound is ethyleneglycol. In embodiments, the oil-immiscible compound is glycerol. Inembodiments, the oil immiscible compound is ethylene glycol, di-ethyleneglycol, propylene glycol, sorbitol, ethanol, isopropanol, secondarybutanol or methanol. In embodiments, the oil immiscible compound isethylene glycol, di-ethylene glycol, propylene glycol, dimethyl ether,pentaerythritol sorbitol, ethanol, isopropanol, secondary butanol ormethanol. In embodiments, the oil-immiscible compound is ethyleneglycol. In embodiments, the oil-immiscible compound is methanol. Inembodiments, the non-aqueous composition includes a surfactant. Wherethe non-aqueous composition includes a surfactant any surfactant usefulin enhanced oil recovery and transport of heavy oil may be used.Examples of surfactants useful for the methods provided have beendescribed above. Where the non-aqueous composition includes anamphiphilic co-solvent any co-solvent useful in enhanced oil recoveryand transport of heavy oil may be used. Examples of co-solvents usefulfor the emulsions and methods provided have been described above (e.g.,a compound of formula (I), (II), (III)).

III. Methods

In another aspect, a method of forming a heavy crude oil emulsion isprovided. The method includes contacting a heavy crude oil extractedfrom an oil reservoir with a co-solvent (e.g., an alkylamine or acompound of formula (I), (II), or (III)) and water at an emulsionforming temperature, thereby forming a high temperature heavy crude oilemulsion. The high temperature heavy crude oil emulsion is allowed tocool to a transport temperature, thereby forming a heavy crude oilemulsion (e.g. an emulsion composition provided herein includingembodiments thereof). The co-solvent is an alkylamine or a compoundhaving the formula:

In formula (I) R^(1A) and R^(1B) are independently hydrogen,unsubstituted C₁-C₈ alkyl, unsubstituted cycloalkyl, unsubstitutedheterocycloalkyl, unsubstituted aryl, unsubstituted heteroaryl, C₁-C₆alkylamine or

R² and R³ are independently hydrogen or unsubstituted C₁-C₂ alkyl. Thesymbol n is an integer from 1 to 30, and m is an integer from 1 to 30.

Where the co-solvent is a compound of formula (I) it may be any compoundaccording to the embodiments provided herein (e.g., a compound offormula (I) wherein R^(1A) and R^(1B) are isopropyl, and R² is hydrogen,and the symbol n is 1 or 3). Thus, in some embodiments, R^(1A) andR^(1B) are independently unsubstituted C₁-C₆ alkyl. In otherembodiments, the number of total carbon atoms within R^(1A) and R^(1B)combined does not exceed 8. In some embodiments, R^(1A) and R^(1B) areindependently unsubstituted C₁-C₄ alkyl. In some embodiments, R^(1A) andR^(1B) are unsubstituted isopropyl. In other embodiments, the symbol nis an integer from 1 to 10. In some embodiments, the symbol n is aninteger from 1 to 6. In some embodiments, R² is hydrogen and n is 1 to3. In other embodiments, the compound has the formula:

In formula (II) R² is methyl or ethyl, o is an integer from 0 to 15, andp is an integer from 1 to 10. In some embodiments, R² is hydrogen, o is0 and p is 1 to 6. In other embodiments, the compound has the formula:

In formula (III) R² is ethyl, q is an integer from 0 to 10, r is aninteger from 0 to 10, and s is an integer from 1 to 10.

Where the co-solvent is an alkylamine it may be any alkylamine providedherein including embodiments thereof (e.g., triethylenetetramine,dimethylaminopropylamine). Thus, in some embodiments, the alkylamine isdiisopropylamine. In other embodiments, the alkylamine is analkylpolyamine. In some embodiments, the alkylpolyamine isdimethylaminopropylamine, triethylenetetramine or diethylenetriamine.

As described above the co-solvent may be present at an amount sufficientto decrease the viscosity of the heavy crude oil. In some embodiments,the co-solvent is present in an amount sufficient to decrease theviscosity of the heavy crude oil at least 1,000-fold. In otherembodiments, the co-solvent is present from about 0.01% to about 5%(w/v).

In some embodiments, the heavy crude oil is present from about 10% toabout 90% (w/v). In some embodiments, the heavy crude oil is presentfrom about 10% to about 95% (w/v). As described above the heavy crudeoil may be present at about 10%, 15%, 20%, 25%, 30%, 35%, 40%, 45%, 50%,55%, 60%, 65%, 70%, 75%, 80%, 85%, 90% or 95% (w/v). In someembodiments, the heavy crude oil is present at about 20% (w/v). In otherembodiments, the heavy crude oil is present at about 40% (w/v). In otherembodiments, the heavy crude oil is present at about 60% (w/v). In otherembodiments, the heavy crude oil is present at about 80% (w/v). A personof ordinary skill in the art will immediately recognize that the abovereferenced values refer to weight percent per volume of emulsion.

As described above the heavy crude oil emulsion provided herein mayinclude an additional co-solvent. Thus, in embodiments, the methodincludes contacting the heavy crude oil extracted from an oil reservoirwith a compound of formula

In formula (IV), L¹ is unsubstituted C₁-C₆ alkylene, unsubstitutedphenylene, unsubstituted cyclohexylene, unsubstituted cyclopentylene ormethyl-substituted cyclopentylene. R² is independently hydrogen, methylor ethyl. R³ is independently hydrogen or

R⁴ is independently hydrogen, methyl or ethyl, n is an integer from 0 to30, and m is an integer from 0 to 30.

In embodiments, the method includes contacting the heavy crude oilextracted from an oil reservoir with a compound of formula

In formula (V) R¹ is independently hydrogen, unsubstituted C₁-C₆ alkylor R⁵—OH, R² is independently hydrogen or unsubstituted C₁-C₂ alkyl, R⁵is independently a bond or unsubstituted C₁-C₆ alkyl, n is an integerfrom 1 to 30, o is an integer from 1 to 5 and z is an integer from 1 to5.

In some embodiments, the method includes contacting the heavy crude oilextracted from an oil reservoir with a compound of formula

In formula (VA) R¹ is independently hydrogen or unsubstituted C₁-C₆alkyl, R² is independently hydrogen or unsubstituted C₁-C₂ alkyl and nis an integer from 1 to 30.

In some embodiments, the method further includes contacting the heavycrude oil extracted from an oil reservoir with an alkali agent. Asdescribed above, an alkali agent as provided herein is a basic, ionicsalt of an alkali metal (e.g. lithium, sodium, potassium) or alkalineearth metal element (e.g. magnesium, calcium, barium, radium). In someembodiments, the alkali agent is NaOH, KOH, LiOH, Na₂CO₃, NaHCO₃,Na-metaborate, Na silicate, Na orthosilicate, or NH₄OH. The emulsioncomposition may include seawater, or fresh water from an aquifer, riveror lake. In some embodiments, the emulsion composition includes hardbrine or soft brine. In some further embodiments, the water is softbrine. In some further embodiments, the water is hard brine. Where theemulsion composition includes soft brine, the aqueous composition mayinclude an alkali agent. In soft brine the alkali agent provides forenhanced soap generation from the oils, lower surfactant adsorption tothe solid material (e.g. rock) in the reservoir and increased solubilityof viscosity enhancing water soluble polymers. In some embodiment, thealkali agent is present in the emulsion composition at a concentrationfrom about 0.1% w/w to about 3% w/w. In some embodiment, the alkaliagent is present in the emulsion composition at a concentration fromabout 0.01% w/w to about 3% w/w. A person of ordinary skill in the artwill immediately recognize that the above referenced values refer toweight percent per weight of aqueous solution.

In some embodiments, the method further includes contacting the heavycrude oil extracted from an oil reservoir with a catalyst. For themethods provided herein any catalyst useful in the process of oilrefining may be used. Examples of catalysts useful for the methodsprovided have been described above.

Using the methods provided herein a heavy crude oil emulsion accordingto the compositions provided herein may be formed. As described abovethe heavy crude oil composition is stable (e.g. maintains a viscositylower than the viscosity of the heavy crude oil) at ambient temperatureand for extended time periods (e.g. weeks, months). In some embodiments,the emulsion is stable at ambient temperature for at least a week. Insome embodiments, the heavy crude oil emulsion is stable at thetransport temperature for at least a week. In other embodiments, theheavy crude oil emulsion is stable at the transport temperature for atleast a month.

As described above the emulsion provided herein is formed at an emulsionforming temperature. The emulsion forming temperature may be equivalentto the temperature of the heavy crude oil in the reservoir. In someembodiments, the emulsion forming temperature is at least 60° C. In someembodiments, the emulsion forming temperature is at least 70° C. Inother embodiments, the emulsion forming temperature is about 100° C. Theheavy crude oil emulsion formed at the emulsion forming temperature isreferred to herein as high temperature heavy crude oil emulsion. Thehigh temperature heavy crude oil emulsion has a viscosity which is lowerthan the heavy crude oil viscosity and may be cooled to a transporttemperature (e.g. ambient temperature). In some embodiments, thetransport temperature is less than 60° C. In other embodiments, thetransport temperature is about 25° C. Surprisingly, after the hightemperature heavy crude oil emulsion is cooled to a transporttemperature, the viscosity of the heavy crude oil emulsion remains lowerthan the viscosity of the heavy crude oil. In some embodiments, theheavy crude oil has a viscosity of at least 100,000 cP. In otherembodiments, the heavy crude oil has a viscosity of at least 200,000 cP.In some embodiments, the heavy crude oil has a viscosity of at least300,000 cP. In some embodiments, the heavy crude oil has a viscosity ofat least 1,000,000 cP. In some embodiments, the extracted heavy crudeoil has a viscosity of at least 100,000 cP at ambient temperature. Inother embodiments, the extracted heavy crude oil has a viscosity of atleast 200,000 cP at ambient temperature. In some embodiments, theextracted heavy crude oil has a viscosity of at least 300,000 cP atambient temperature. In some embodiments, the extracted heavy crude oilhas a viscosity of at least 1,000,000 cP at ambient temperature. Theviscosity of the heavy crude oil emulsion may be 1,000 times lower thanthe viscosity of the heavy crude oil. In some embodiments, the viscosityof the heavy crude oil emulsion is 10,000 times lower than the viscosityof the heavy crude oil. In other embodiments, the viscosity of the heavycrude oil emulsion is 100,000 times lower than the viscosity of theheavy crude oil.

In another aspect, a method of optimizing a heavy crude oil emulsion isprovided. The method includes contacting a plurality of heavy crude oilsamples extracted from an oil reservoir with an amount of a co-solvent,an amount of a salt and an amount of water at an emulsion formingtemperature, wherein the amount of a co-solvent, the amount of a saltand the amount of water is different for each of the plurality of heavycrude oil samples, thereby forming a plurality of different hightemperature heavy crude oil emulsion samples. The plurality of differenthigh temperature heavy crude oil emulsion samples is allowed to cool toan ambient temperature, thereby forming a plurality of different lowtemperature heavy crude oil emulsion samples. A low temperature heavycrude oil emulsion sample is identified amongst the plurality ofdifferent low temperature heavy crude oil emulsion samples having aviscosity at least 100 times lower than the viscosity of the heavy crudeoil, thereby optimizing a heavy crude oil emulsion. The co-solvent is analkylamine or a compound having the formula:

In formula (I) R^(1A) and R^(1B) are independently hydrogen,unsubstituted C₁-C₈ alkyl, unsubstituted cycloalkyl, unsubstitutedheterocycloalkyl, unsubstituted aryl, unsubstituted heteroaryl, C₁-C₆alkylamine or

R² and R³ are independently hydrogen or unsubstituted C₁-C₂ alkyl. Thesymbol n is an integer from 1 to 30, and m is an integer from 1 to 30.In some embodiments, the amount of a co-solvent is from about 0.01% toabout 5% (w/v). In other embodiments, the amount of a basic agent isfrom about 0.01% to about 3% (w/v). In some embodiments, the amount ofwater is from about 1% to about 90% (w/v). In some embodiments, theheavy crude oil emulsion is stable at a shear rate from about 0.01 toabout 100,000 reciprocal seconds.

In another aspect, a method of transporting a heavy crude oil isprovided. The method includes extracting a heavy crude oil from an oilreservoir, thereby forming an extracted heavy crude oil. The extractedheavy crude oil is contacted with a co-solvent and water at an emulsionforming temperature, thereby forming a high temperature heavy crude oilemulsion. The high temperature heavy crude oil emulsion is allowed tocool to a transport temperature, thereby forming a heavy crude oilemulsion. The heavy crude oil emulsion is transported from a firstlocation to a second location, thereby transporting the heavy crude oil.The co-solvent is an alkylamine or a compound having the formula:

In formula (I) R^(1A) and R^(1B) are independently hydrogen,unsubstituted C₁-C₈ alkyl, unsubstituted cycloalkyl, unsubstitutedheterocycloalkyl, unsubstituted aryl, unsubstituted heteroaryl, C₁-C₆alkylamine or

R² and R³ are independently hydrogen or unsubstituted C₁-C₂ alkyl. Thesymbol n is an integer from 1 to 30 and m is an integer from 1 to 30. Inanother embodiment, the method further includes contacting the extractedheavy crude oil with a catalyst. In some embodiments, the transportingof step (iv) is performed in a vessel. In other embodiments, the vesselis a pipeline. In some embodiments, the vessel forms part of atransportation vehicle. In other embodiments, the method furtherincludes after the transporting of step (iv) separating the heavy crudeoil from the co-solvent and the water, thereby forming a recovered heavycrude oil.

In another aspect, a method of forming a heavy crude oil emulsion in aproduction well is provided. The method includes contacting an extractedheavy crude oil in a production well with a co-solvent (e.g., a compoundof formula (I), (II), (III) or an alkylamine) and water, thereby forminga heavy crude oil emulsion in the production well. The co-solvent is analkylamine or a compound having the formula:

In formula (I) R^(1A) and R^(1B) are independently hydrogen,unsubstituted C₁-C₈ alkyl, unsubstituted cycloalkyl, unsubstitutedheterocycloalkyl, unsubstituted aryl, unsubstituted heteroaryl, C₁-C₆alkylamine or

R² and R³ are independently hydrogen or unsubstituted C₁-C₂ alkyl, n isan integer from 1 to 30 and m is an integer from 1 to 30.

In embodiments, the alkylamine is diisopropylamine. In otherembodiments, the alkylamine is an alkylpolyamine. In some embodiments,the alkylpolyamine is dimethylaminopropylamine, triethylenetetramine ordiethylenetriamine.

In some embodiments, the extracted heavy crude oil is present from about10% to about 95% (w/v). The extracted heavy crude oil may be present atabout 10%, 15%, 20%, 25%, 30%, 35%, 40%, 45%, 50%, 55%, 60%, 65%, 70%,75%, 80%, 85%, 90% or 95% (w/v). In some embodiments, the extractedheavy crude oil is present at about 20% (w/v). In other embodiments, theextracted heavy crude oil is present at about 40% (w/v). In otherembodiments, the extracted heavy crude oil is present at about 60%(w/v). In other embodiments, the extracted heavy crude oil is present atabout 80% (w/v). A person of ordinary skill in the art will immediatelyrecognize that the above referenced values refer to weight percent pervolume of emulsion. The emulsion provided herein is formed at anemulsion forming temperature. The emulsion forming temperature may beequivalent to the temperature of the heavy crude oil in the reservoir.In some embodiments, the emulsion forming temperature is at least 60° C.In some embodiments, the emulsion forming temperature is at least 70° C.In other embodiments, the emulsion forming temperature is about 100° C.

In some embodiments, the heavy crude oil emulsion is stable at thetransport temperature for at least an hour. In some embodiments, theheavy crude oil emulsion is stable at the transport temperature for atleast a day. In some embodiments, the heavy crude oil emulsion is stableat the transport temperature for at least a week. In other embodiments,the heavy crude oil emulsion is stable at the transport temperature forat least a month.

In some embodiments, the extracted heavy crude oil has a viscosity of atleast 100,000 cP. In other embodiments, the extracted heavy crude oilhas a viscosity of at least 200,000 cP. In some embodiments, theextracted heavy crude oil has a viscosity of at least 300,000 cP. Insome embodiments, the extracted heavy crude oil has a viscosity of atleast 1,000,000 cP. In some embodiments, the extracted heavy crude oilhas a viscosity of at least 100,000 cP at ambient temperature. In otherembodiments, the extracted heavy crude oil has a viscosity of at least200,000 cP at ambient temperature. In some embodiments, the extractedheavy crude oil has a viscosity of at least 300,000 cP at ambienttemperature. In some embodiments, the extracted heavy crude oil has aviscosity of at least 1,000,000 cP at ambient temperature. The viscosityof the heavy crude oil emulsion may be 1,000 times lower than theviscosity of the extracted heavy crude oil. In some embodiments, theviscosity of the heavy crude oil emulsion is 10,000 times lower than theviscosity of the extracted heavy crude oil. In other embodiments, theviscosity of the heavy crude oil emulsion is 100,000 times lower thanthe viscosity of the extracted heavy crude oil.

The heavy crude oil emulsion provided herein may be formed in aproduction well by contacting the extracted heavy crude oil with anadditional co-solvent. Thus, in embodiments, the method includescontacting the extracted heavy crude oil with a compound of formula

In formula (IV), L¹ is unsubstituted C₁-C₆ alkylene, unsubstitutedphenylene, unsubstituted cyclohexylene, unsubstituted cyclopentylene ormethyl-substituted cyclopentylene. R² is independently hydrogen, methylor ethyl. R³ is independently hydrogen or

R⁴ is independently hydrogen, methyl or ethyl, n is an integer i from 0to 30, and m is an integer from 0 to 30.

In embodiments, the method includes contacting the extracted heavy crudeoil with a compound of formula

In formula (V) R¹ is independently hydrogen, unsubstituted C₁-C₆ alkylor R⁵—OH, R² is independently hydrogen or unsubstituted C₁-C₂ alkyl, R⁵is independently a bond or unsubstituted C₁-C₆ alkyl, n is an integerfrom 1 to 30, o is an integer from 1 to 5 and z is an integer from 1 to5.

In some embodiments, the method includes contacting the extracted heavycrude oil with a compound of formula

In formula (VA) R¹ is independently hydrogen or unsubstituted C₁-C₆alkyl, R² is independently hydrogen or unsubstituted C₁-C₂ alkyl and nis an integer from 1 to 30.

In embodiments, the extracted heavy crude oil is contacted with asurfactant. In embodiments, the extracted heavy crude oil is contactedwith a catalyst. In embodiments, the co-solvent is a compound of formula(I) (II), (III) or an alkylamine. In embodiments, the co-solvent is aco-solvent blend. In embodiments, the co-solvent is present at aconcentration from about 0.01% w/w to about 5% w/w. A person of ordinaryskill in the art will immediately recognize that the above referencedvalues for the concentration of co-solvent refer to weight percent pervolume of water and oil combined (i.e. emulsion).

In another aspect, a method of transporting an extracted heavy crude oilfrom a production well is provided. The method includes contacting anextracted heavy crude oil in a production well with a co-solvent, andwater at an emulsion forming temperature, thereby forming a heavy crudeoil emulsion in a production well. The heavy crude oil emulsion istransported from the production well to the surface, therebytransporting the extracted heavy crude oil from the production well. Theco-solvent is an alkylamine or a compound having the formula:

In formula (I) R^(1A) and R^(1B) are independently hydrogen,unsubstituted C₁-C₈ alkyl, unsubstituted cycloalkyl, unsubstitutedheterocycloalkyl, unsubstituted aryl, unsubstituted heteroaryl, C₁-C₆alkylamine or

R² and R³ are independently hydrogen or unsubstituted C₁-C₂ alkyl, n isan integer from 1 to 30 and m is an integer from 1 to 30. Inembodiments, the method includes contacting the extracted heavy crudeoil with an additional co-solvent. In embodiments, the additionalco-solvent is a compound of formula ((IV), (IVA), (IVB), (IVC), (IVD),(V), (VA), or (VB))). In embodiments, the method includes contacting theextracted heavy crude oil with a co-solvent blend. In embodiments, theextracted heavy crude oil is contacted with a surfactant. Inembodiments, the transporting of step (ii) includes moving the heavycrude oil transport emulsion with a mechanical pump. In embodiments, themechanical pump is an electrical submersible pump.

In another aspect, a method of forming a heavy crude oil emulsion isprovided. The method includes contacting a heavy crude oil extractedfrom an oil reservoir with an oil-immiscible compound and an amphiphilicco-solvent at an emulsion forming temperature, thereby forming a hightemperature heavy crude oil emulsion. The high temperature heavy crudeoil emulsion is allowed to cool to a transport temperature, therebyforming a heavy crude oil emulsion. The amphiphilic co-solvent is analkylamine (e.g., diisopropylamine, alkylpolyamine,dimethylaminopropylamine, triethylenetetramine or diethylenetriamine) ora compound having the formula:

In formula (I) R^(1A) and R^(1B) are independently hydrogen,unsubstituted C₁-C₈ alkyl, unsubstituted cycloalkyl, unsubstitutedheterocycloalkyl, unsubstituted aryl, unsubstituted heteroaryl, C₁-C₆alkylamine or

R² and R³ are independently hydrogen or unsubstituted C₁-C₂ alkyl, n isan integer from 1 to 30 and m is an integer from 1 to 30. Inembodiments, the oil immiscible compound is ethylene glycol, di-ethyleneglycol, glycerol, propylene glycol, pentaerythritol, sorbitol ormethanol. In embodiments, the oil-immiscible compound is ethyleneglycol. In embodiments, the oil-immiscible compound is glycerol. Inembodiments, the oil immiscible compound is ethylene glycol, di-ethyleneglycol, propylene glycol, sorbitol, ethanol, isopropanol, secondarybutanol or methanol. In embodiments, the oil-immiscible compound isethylene glycol. In embodiments, the oil-immiscible compound ismethanol. In embodiments, the oil immiscible compound is ethyleneglycol, di-ethylene glycol, propylene glycol, dimethyl ether,pentaerythritol sorbitol, ethanol, isopropanol, secondary butanol ormethanol.

In embodiments, the amount of water in the heavy crude oil emulsion isequal to the amount of water in the extracted heavy crude oil. Inembodiments, the heavy crude oil emulsion does not include water. Inembodiments, the heavy crude oil emulsion does not include added water.In embodiments, the heavy crude oil emulsion is anhydrous. Inembodiments, the extracted heavy crude oil emulsion includes heavy crudeoil water. In embodiments, the amount of water in the heavy crude oilemulsion is equal to the amount of the heavy crude oil water. Inembodiments, the heavy crude oil emulsion includes traces of water.Where the heavy crude oil emulsion includes traces of water, the heavycrude oil emulsion includes less than about 0.01% (w/v) water. Inembodiments, the heavy crude oil emulsion includes less than about 20%(w/v) water. In embodiments, the heavy crude oil emulsion includes lessthan about 15% (w/v) water. In embodiments, the heavy crude oil emulsionincludes less than about 10% (w/v) water. In embodiments, the heavycrude oil emulsion includes less than about 5% (w/v) water. Inembodiments, the heavy crude oil emulsion includes less than about 4%(w/v) water. In embodiments, the heavy crude oil emulsion includes lessthan about 3% (w/v) water. In embodiments, the heavy crude oil emulsionincludes less than about 2% (w/v) water. In embodiments, the heavy crudeoil emulsion includes less than about 1% (w/v) water. In embodiments,the heavy crude oil emulsion includes less than about 0.5% (w/v) water.In embodiments, the heavy crude oil emulsion includes less than about0.4% (w/v) water. In embodiments, the heavy crude oil emulsion includesless than about 0.3% (w/v) water. In embodiments, the heavy crude oilemulsion includes less than about 0.2% (w/v) water. In embodiments, theheavy crude oil emulsion includes less than about 0.1% (w/v) water. Inembodiments, the heavy crude oil emulsion includes less than about 0.01%(w/v) water. In embodiments, the heavy crude oil emulsion includes lessthan about 20% (w/v) water. In embodiments, the heavy crude oil emulsionincludes less than about 15% (w/v) water. In embodiments, the heavycrude oil emulsion includes less than about 10% (w/v) water. Inembodiments, the amount of the heavy crude oil water is less than about5% (w/v). In embodiments, the amount of the heavy crude oil water isless than about 2% (w/v). In embodiments, the amount of the heavy crudeoil water is less than about 1% (w/v). In embodiments, the amount ofwater in the heavy crude oil emulsion is equal to the amount of theheavy crude oil water. A person of ordinary skill in the art willimmediately recognize that the above referenced values refer to weightpercent per volume of emulsion. In embodiments, the extracted heavycrude oil is contacted with a surfactant.

In another aspect, a method of forming a heavy crude oil emulsion in aproduction well is provided. The method includes contacting an extractedheavy crude oil in a production well with an oil-immiscible compound andan amphiphilic co-solvent, thereby forming a heavy crude oil emulsion ina production well. The amphiphilic co-solvent is an alkylamine (e.g.,diisopropylamine, alkylpolyamine, dimethylaminopropylamine,triethylenetetramine or diethylenetriamine) or a compound having theformula:

In formula (I) R^(1A) and R^(1B) are independently hydrogen,unsubstituted C₁-C₈ alkyl, unsubstituted cycloalkyl, unsubstitutedheterocycloalkyl, unsubstituted aryl, unsubstituted heteroaryl, C₁-C₆alkylamine or

R² and R³ are independently hydrogen or unsubstituted C₁-C₂ alkyl, n isan integer from 1 to 30 and m is an integer from 1 to 30. Inembodiments, the oil immiscible compound is ethylene glycol, di-ethyleneglycol, glycerol, propylene glycol, pentaerythritol, sorbitol ormethanol. In embodiments, the oil-immiscible compound is ethyleneglycol. In embodiments, the oil-immiscible compound is glycerol. Inembodiments, the oil immiscible compound is ethylene glycol, di-ethyleneglycol, propylene glycol, sorbitol, ethanol, isopropanol, secondarybutanol or methanol. In embodiments, the oil-immiscible compound isethylene glycol. In embodiments, the oil-immiscible compound ismethanol. In embodiments, the oil immiscible compound is ethyleneglycol, di-ethylene glycol, propylene glycol, dimethyl ether,pentaerythritol sorbitol, ethanol, isopropanol, secondary butanol ormethanol.

In embodiments, the amount of water in the heavy crude oil emulsion isequal to the amount of water in the extracted heavy crude oil. Inembodiments, the heavy crude oil emulsion does not include water. Inembodiments, the heavy crude oil emulsion does not include added water.In embodiments, the heavy crude oil emulsion is anhydrous. Inembodiments, the extracted heavy crude oil emulsion includes heavy crudeoil water. In embodiments, the amount of water in the heavy crude oilemulsion is equal to the amount of the heavy crude oil water. Inembodiments, the heavy crude oil emulsion includes traces of water.Where the heavy crude oil emulsion includes traces of water, the heavycrude oil emulsion includes less than about 0.01% (w/v) water. Inembodiments, the heavy crude oil emulsion includes less than about 20%(w/v) water. In embodiments, the heavy crude oil emulsion includes lessthan about 15% (w/v) water. In embodiments, the heavy crude oil emulsionincludes less than about 10% (w/v) water. In embodiments, the heavycrude oil emulsion includes less than about 5% (w/v) water. Inembodiments, the heavy crude oil emulsion includes less than about 4%(w/v) water. In embodiments, the heavy crude oil emulsion includes lessthan about 3% (w/v) water. In embodiments, the heavy crude oil emulsionincludes less than about 2% (w/v) water. In embodiments, the heavy crudeoil emulsion includes less than about 1% (w/v) water. In embodiments,the heavy crude oil emulsion includes less than about 0.5% (w/v) water.In embodiments, the heavy crude oil emulsion includes less than about0.4% (w/v) water. In embodiments, the heavy crude oil emulsion includesless than about 0.3% (w/v) water. In embodiments, the heavy crude oilemulsion includes less than about 0.2% (w/v) water. In embodiments, theheavy crude oil emulsion includes less than about 0.1% (w/v) water. Inembodiments, the heavy crude oil emulsion includes less than about 0.01%(w/v) water. In embodiments, the heavy crude oil emulsion includes lessthan about 20% (w/v) water. In embodiments, the heavy crude oil emulsionincludes less than about 15% (w/v) water. In embodiments, the heavycrude oil emulsion includes less than about 10% (w/v) water. Inembodiments, the amount of the heavy crude oil water is less than about5% (w/v). In embodiments, the amount of the heavy crude oil water isless than about 2% (w/v). In embodiments, the amount of the heavy crudeoil water is less than about 1% (w/v). In embodiments, the amount ofwater in the heavy crude oil emulsion is equal to the amount of theheavy crude oil water. A person of ordinary skill in the art willimmediately recognize that the above referenced values refer to weightpercent per volume of emulsion. In embodiments, the extracted heavycrude oil is contacted with a surfactant.

In another aspect, a method of transporting an extracted heavy crude oilfrom a production well is provided. The method includes contacting anextracted heavy crude oil in a production well with an oil-immisciblecompound and an amphiphilic co-solvent at an emulsion formingtemperature, thereby forming a heavy crude oil emulsion in a productionwell. The heavy crude oil emulsion is transported from the productionwell to the surface, thereby transporting the extracted heavy crude oilfrom the production well. The amphiphilic co-solvent is an alkylamine(e.g., diisopropylamine, alkylpolyamine, dimethylaminopropylamine,triethylenetetramine or diethylenetriamine) or a compound having theformula:

In formula (I) R^(1A) and R^(1B) are independently hydrogen,unsubstituted C₁-C₈ alkyl, unsubstituted cycloalkyl, unsubstitutedheterocycloalkyl, unsubstituted aryl, unsubstituted heteroaryl, C₁-C₆alkylamine or

R² and R³ are independently hydrogen or unsubstituted C₁-C₂ alkyl, n isan integer from 1 to 30 and m is an integer from 1 to 30. Inembodiments, the oil immiscible compound is ethylene glycol, di-ethyleneglycol, glycerol, propylene glycol, pentaerythritol, sorbitol ormethanol. In embodiments, the oil-immiscible compound is ethyleneglycol. In embodiments, the oil-immiscible compound is glycerol. Inembodiments, the oil immiscible compound is ethylene glycol, di-ethyleneglycol, propylene glycol, sorbitol, ethanol, isopropanol, secondarybutanol or methanol. In embodiments, the oil-immiscible compound isethylene glycol. In embodiments, the oil-immiscible compound ismethanol. In embodiments, the oil immiscible compound is ethyleneglycol, di-ethylene glycol, propylene glycol, dimethyl ether,pentaerythritol sorbitol, ethanol, isopropanol, secondary butanol ormethanol.

In embodiments, the amount of water in the heavy crude oil emulsion isequal to the amount of water in the extracted heavy crude oil. Inembodiments, the heavy crude oil emulsion does not include water. Inembodiments, the heavy crude oil emulsion does not include added water.In embodiments, the heavy crude oil emulsion is anhydrous. Inembodiments, the extracted heavy crude oil emulsion includes heavy crudeoil water. In embodiments, the amount of water in the heavy crude oilemulsion is equal to the amount of the heavy crude oil water. Inembodiments, the heavy crude oil emulsion includes traces of water.Where the heavy crude oil emulsion includes traces of water, the heavycrude oil emulsion includes less than about 0.01% (w/v) water. Inembodiments, the heavy crude oil emulsion includes less than about 20%(w/v) water. In embodiments, the heavy crude oil emulsion includes lessthan about 15% (w/v) water. In embodiments, the heavy crude oil emulsionincludes less than about 10% (w/v) water. In embodiments, the heavycrude oil emulsion includes less than about 5% (w/v) water. Inembodiments, the heavy crude oil emulsion includes less than about 4%(w/v) water. In embodiments, the heavy crude oil emulsion includes lessthan about 3% (w/v) water. In embodiments, the heavy crude oil emulsionincludes less than about 2% (w/v) water. In embodiments, the heavy crudeoil emulsion includes less than about 1% (w/v) water. In embodiments,the heavy crude oil emulsion includes less than about 0.5% (w/v) water.In embodiments, the heavy crude oil emulsion includes less than about0.4% (w/v) water. In embodiments, the heavy crude oil emulsion includesless than about 0.3% (w/v) water. In embodiments, the heavy crude oilemulsion includes less than about 0.2% (w/v) water. In embodiments, theheavy crude oil emulsion includes less than about 0.1% (w/v) water. Inembodiments, the heavy crude oil emulsion includes less than about 0.01%(w/v) water. In embodiments, the heavy crude oil emulsion includes lessthan about 20% (w/v) water. In embodiments, the heavy crude oil emulsionincludes less than about 15% (w/v) water. In embodiments, the heavycrude oil emulsion includes less than about 10% (w/v) water. Inembodiments, the amount of the heavy crude oil water is less than about5% (w/v). In embodiments, the amount of the heavy crude oil water isless than about 2% (w/v). In embodiments, the amount of the heavy crudeoil water is less than about 1% (w/v). In embodiments, the amount ofwater in the heavy crude oil emulsion is equal to the amount of theheavy crude oil water. A person of ordinary skill in the art willimmediately recognize that the above referenced values refer to weightpercent per volume of emulsion. In embodiments, the extracted heavycrude oil is contacted with a surfactant.

IV. Examples

Applicants have discovered that certain amine and amine alkoxylateco-solvents (e.g., alkylamine or a compound of formula (I), (II), or(III)) are superior to the use of alkali only or surfactant only ordiluent (solvent) only. Such co-solvents promote the formation oflow-viscosity microemulsions as well as low viscosity macroemulsions.Furthermore, such co-solvent physically disrupts the asphaltenes inheavy crude oils by interacting with the resins that stabilize theasphaltenes. The amine and amine alkoxylate co-solvents may directlyinteract with asphaltenes and cause disruptions of intermolecularaggregations. Remarkably low concentrations of certain tailoredco-solvents are effective in this regard. Depending on the crude oilproperties, it is sometimes necessary to first moderately increase thetemperature of the mixture of co-solvent, brine and heavy oil to formthe emulsions, but they do not need to be kept hot since the viscosityremains low when the temperature is lowered. In many cases, thermalmethods such as steam are used to extract heavy oil from the reservoirso the oil will already be hot when it reaches the surface and thus noheating will be necessary.

Phase Behavior Procedures

Phase Behavior Screening: Phase behavior studies have been used tocharacterize chemicals for EOR. There are many benefits in using phasebehavior as a screening method. Phase Behavior studies are used todetermine the effect of electrolytes, co-solvents, alkalis, surfactants,polymers, temperature, pressure and other variables on: (1) IFTreduction; (2) oil solubilization ratios, (3) microemulsion densities;(4) microemulsion viscosities; (5) coalescence times; (6) interfacialviscosity (7) optimal properties for recovering oil from cores andreservoirs.

Thermodynamically stable phases can form with oil, water andnon-surfactant aqueous mixtures. In situ generated soaps form micellarstructures at concentrations at or above the critical micelleconcentration (CMC). The emulsion coalesces into a separate phase at theoil-water interface and is referred to as a microemulsion. Amicroemulsion is a surfactant-rich or soap-rich distinct phaseconsisting of in situ generated soaps, oil, water and co-solvent, alkaliagent and other components. This phase is thermodynamically stable inthe sense that it will return to the same phase volume at a giventemperature. Some workers in the past have added additionalrequirements, but for the purposes of this engineering study, the onlyrequirement will be that the microemulsion is a thermodynamically stablephase.

The phase transition is examined by keeping all variables fixed exceptfor the scanning variable. The scan variable is changed over a series ofpipettes and may include, but is not limited to, salinity, temperature,chemical (co-solvent, alcohol, electrolyte), oil, which is sometimescharacterized by its equivalent alkane carbon number (EACN), andco-solvent structure, which is sometimes characterized by itshydrophilic-lipophilic balance (HLB). The phase transition was firstcharacterized by Winsor (1954) into three regions: Type I—excess oleicphase, Type III—aqueous, microemulsion and oleic phases, and the TypeII—excess aqueous phase. The phase transition boundaries and some commonterminology are described as follows: Type I to III—lower criticalsalinity, Type III to II—upper critical salinity, oil solubilizationratio (Vo/Vs), water solubilization ratio (Vw/Vs), the solubilizationvalue where the oil and water solubilization ratios are equal is calledthe Optimum Solubilization Ratio (σ*), and the electrolyte concentrationwhere the optimum solubilization ratio occurs is referred to as theOptimal Salinity (S*). Since no surfactant is added, the only surfactantpresent is the in-situ generated soap. For the purpose of calculating asolubilization ratio, one can assume a value for soap level using TAN(total acid number) and an approximate molecular weight for the soap.

Determining Interfacial Tension

Efficient use of time and lab resources can lead to valuable resultswhen conducting phase behavior scans. A correlation between oil andwater solubilization ratios and interfacial tension was suggested byHealy and Reed (1976) and a theoretical relationship was later derivedby Chun Huh (1979). Lowest oil-water IFT occurs at optimumsolubilization as shown by the Chun Huh theory. This is equated to aninterfacial tension through the Chun Huh equation, where IFT varies withthe inverse square of the solubilization ratio:

$\begin{matrix}{\gamma = \frac{C}{\sigma^{2}}} & (1)\end{matrix}$

For most crude oils and microemulsions, C=0.3 is a good approximation.Therefore, a quick and convenient way to estimate IFT is to measurephase behavior and use the Chun-Huh equation to calculate IFT. The IFTbetween microemulsions and water and/or oil can be very difficult andtime consuming to measure and is subject to larger errors, so using thephase behavior approach to screen hundreds of combinations ofco-solvents, electrolytes, oil, and so forth is not only simpler andfaster, but avoids the measurement problems and errors associated withmeasuring IFT especially of combinations that show complex behavior(gels and so forth) and will be screened out anyway. Once a goodformulation has been identified, then it is still a good idea to measureIFT.

Equipment

Phase behavior experiments are created with the following materials andequipment.

Mass Balance: Mass balances are used to measure chemicals for mixturesand determine initial saturation values of cores.

Water Deionizer: Deionized (DI) water is prepared for use with all theexperimental solutions using a Nanopure™ filter system. This filter usesa recirculation pump and monitors the water resistivity to indicate whenthe ions have been removed. Water is passed through a 0.45 micron filterto eliminate undesired particles and microorganisms prior to use.

Borosilicate Pipettes: Standard 5 mL borosilicate pipettes with 0.1 mLmarkings are used to create phase behavior scans as well as run dilutionexperiments with aqueous solutions. Ends are sealed using a propane andoxygen flame.

Pipette Repeater: An Eppendorf Repeater Plus® instrument is used formost of the pipetting. This is a handheld dispenser calibrated todeliver between 25 microliter and 1 ml increments. Disposable tips areused to avoid contamination between stocks and allow for ease ofoperation and consistency.

Propane-oxygen Torch: A mixture of propane and oxygen gas is directedthrough a Bernz-O-Matic flame nozzle to create a hot flame about ½ inchlong. This torch is used to flame-seal the glass pipettes used in phasebehavior experiments.

Convection Ovens: Several convection ovens are used to incubate thephase behaviors and core flood experiments at the reservoirtemperatures. The phase behavior pipettes are primarily kept in Blue Mand Memmert ovens that are monitored with mercury thermometers and oventemperature gauges to ensure temperature fluctuations are kept at aminimal between recordings. A large custom built flow oven was used tohouse most of the core flood experiments and enabled fluid injection andcollection to be done at reservoir temperature.

pH Meter: An ORION research model 701/digital ion analyzer with a pHelectrode is used to measure the pH of most aqueous samples to obtainmore accurate readings. This is calibrated with 4.0, 7.0 and 10.0 pHsolutions. For rough measurements of pH, indicator papers are used withseveral drops of the sampled fluid.

Phase Behavior Calculations

The oil and water solubilization ratios are calculated from interfacemeasurements taken from phase behavior pipettes. These interfaces arerecorded over time as the mixtures approached equilibrium and the volumeof any macroemulsions that initially formed decreased or disappeared.

Phase Behavior Methodology

The methods for creating, measuring and recording observations aredescribed in this section. Scans are made using a variety of electrolytemixtures described below. Oil is added to most aqueous non-surfactantsolutions to see if a microemulsion formed, how long it took to form andequilibrate if it formed, what type of microemulsion formed and some ofits properties such as viscosity. However, the behavior of aqueousmixtures without oil added is also important and is also done in somecases to determine if the aqueous solution is clear and stable overtime, becomes cloudy or separated into more than one phase.

Preparation of samples. Phase behavior samples are made by firstpreparing non-surfactant aqueous stock solutions and combining them withbrine stock solutions in order to observe the behavior of the mixturesover a range of salinities.

Solution Preparation. Non-surfactant aqueous stock solutions are basedon active weight-percent co-solvent. The masses of co-solvent, alkaliagent and de-ionized water (DI) are measured out on a balance and mixedin glass jars using magnetic stir bars. The order of addition isrecorded on a mixing sheet along with actual masses added and the pH ofthe final solution. Brine solutions are created at the necessary weightpercent concentrations for making the scans.

Co-solvent Stock. The chemicals being tested are first mixed in aconcentrated stock solution that usually consisted of co-solvent, alkaliagent and/or polymer along with de-ionized water. The quantity ofchemical added is calculated based on activity and measured by weightpercent of total solution. Initial experiments are at about 1-3%co-solvent so that the volume of the middle microemulsion phase would belarge enough for accurate measurements assuming a solubilization ratioof at least 10 at optimum salinity.

Polymer Stock. Often these stocks were quite viscous and made pipettingdifficult so they are diluted with de-ionized water accordingly toimprove ease of handling. Mixtures with polymer are made only for thoseco-solvent formulations that showed good behavior and merited additionalstudy for possible testing in core floods. Consequently, scans includingpolymer are limited since they are done only as a final evaluation ofcompatibility with the co-solvent.

Pipetting Procedure. Phase behavior components are added volumetricallyinto 5 ml pipettes using an Eppendorf Repeater Plus or similar pipettinginstrument. Co-solvent, alkali agent and brine stocks are mixed with DIwater into labeled pipettes and brought to temperature before agitation.Almost all of the phase behavior experiments are initially created witha water oil ratio (WOR) of 1:1, which involves mixing 2 ml of theaqueous phase with 2 ml of the evaluated crude oil or hydrocarbon, anddifferent WOR experiments are mixed accordingly. The typical phasebehavior scan consisted of 10-20 pipettes, each pipette being recognizedas a data point in the series.

Order of Addition. Consideration must be given to the addition of thecomponents since the concentrations are often several folds greater thanthe final concentration. Therefore, an order is established to preventany adverse effects resulting from co-solvent, alkali agent or polymercoming into direct contact with the concentrated electrolytes. Thedesired sample compositions are made by combining the stocks in thefollowing order: (1) Electrolyte stock(s); (2) De-ionized water; (3)co-solvent stock; (4) alkali agent stock; (5) Polymer stock; and (6)Crude oil or hydrocarbon.

Initial Observations. Once the components are added to the pipettes,sufficient time is allotted to allow all the fluid to drain down thesides. Then aqueous fluid levels are recorded before the addition ofoil. These measurements are marked on record sheets. Levels andinterfaces are recorded on these documents with comments over severaldays and additional sheets are printed as necessary.

Sealing and Mixing. The pipettes are blanketed with argon gas to preventthe ignition of any volatile gas present by the flame sealing procedure.The tubes are then sealed with the propane-oxygen torch to prevent lossof additional volatiles when placed in the oven. Pipettes are arrangedon the racks to coincide with the change in the scan variable. Once thephase behavior scan is given sufficient time to reach reservoirtemperature (15-30 minutes), the pipettes are inverted several times toprovide adequate mixing. Tubes are observed for low tension upon mixingby looking at droplet size and how uniform the mixture appeared. Thenthe solutions are allowed to equilibrate over time and interface levelsare recorded to determine equilibration time and co-solvent/alkali agentperformance.

Measurements and Observations. Phase behavior experiments are allowed toequilibrate in an oven that is set to the reservoir temperature for thecrude oil being tested. The fluid levels in the pipettes are recordedperiodically and the trend in the phase behavior observed over time.Equilibrium behavior is assumed when fluid levels ceased to changewithin the margin of error for reading the samples.

Fluid Interfaces. The fluid interfaces are the most crucial element ofphase behavior experiments. From them, the phase volumes are determinedand the solubilization ratios are calculated. The top and bottominterfaces are recorded as the scan transitioned from an oil-in-watermicroemulsion to a water-in-oil microemulsion. Initial readings aretaken one day after initial agitation and sometimes within hours ofagitation if coalescence appeared to happen rapidly. Measurements aretaken thereafter at increasing time intervals (for example, one day,four days, one week, two weeks, one month and so on) until equilibriumis reached or the experiment is deemed unessential or uninteresting forcontinued observation.

Emulsion Preparation Procedure

The stock solutions listed below are prepared as follows:

a. Alkali Solution (optional)

b. Brine solution

c. Co-solvent Solution

Pipet the required volume of the stock solutions to get a solution withspecified alkali, brine, and co-solvent concentrations. Pipet therequired volume of the aqueous solution into a 50 ml glass centrifugetube. Pipet the required volume of the oil into the glass centrifugetube. Cap the centrifuge tube and put the samples into a 100° C. oven.After the samples are at the oven temperature, mix (hand shake) thesamples well every 20 minutes for 2 hour. The samples are mixed approx.15-30 seconds. Take the samples out of the oven and let them reach roomtemperature (˜25° C.).

Viscosity Measurement Procedure

Briefly mix (hand shake) the emulsion sample and pour it into a 25 mlcolumn. Using mineral oil and Teledyne ISCO 500D Series Syringe Pump,inject the mineral oil into the 25 ml column and displace the emulsioninto the capillary tube at constant volumetric flow rates. The mixingbetween the mineral oil and emulsion seemed to be minimal. When a flowrate is inputted into the pump, check the pressure drop across thecapillary tube every 30 seconds using a transducer that is connected tothe LabView program. Wait until steady state pressure drop is observedand recorded the pressure drop. Change the flow rate and repeat tomeasure a range of shear rates by varying the flow rate.

Experimental Procedure for Emulsion Breaking

Acid such as sulfuric acid, hydrochloric acid is administered to theheavy oil emulsion to neutralize the alkali initially added to createthe emulsion and to return the pH from neutral to acidic. The sample isshaken and allowed sufficient time to convert the soap produced from theheavy oil back to the acidic components of the oil. The temperature ofthe sample may be increased to improve the kinetics of the reaction. Thesample is briefly centrifuged to separate the demulsified heavy oil fromthe aqueous solution (water, salt, co-solvent). In some embodiments,methods known in the art for breaking a heavy crude oil emulsion areused. Useful methods of breaking an emulsion are for example disclosedin Verzaro et al. (2002; SPE/Petroleum Society of CIM/CHOA 78959, page1-5).

Upgrading of Heavy Oil During Transportation (Formation of Reformate)

Nanoparticle Catalyst Upgrading in Pipeline

Catalytic nanoparticles have larger surface area per mass for reactionsto occur, thus requiring smaller quantity. The property of nanoparticlesto prefer to be in the interface of oil and water is advantageous andnecessary for the heavy oil upgrading because of the emulsiontransportation method claimed. The catalytic nanoparticles areincorporated into the emulsion along with water, alkaline, andco-solvent and transported through pipeline, ending with the separationof the catalyst for possible reuse. Several examples of catalysts anddifferent reactions for upgrading oil (forming reformates) are listedbelow.

Hydrogenation and Hydrogenolysis Reactions Via H₂ Transfer

Catalysts used are platinum, palladium, rhodium or nickel.

Dehydrogenation and Metathesis Reactions Via Loss of H₂ from OilMolecules

Catalysts used are chromium oxide, Pt/Al₂O₃, or zinc titanium oxide.

Hydrocracking Reaction

Breaking of carbon-carbon bond to create smaller oil molecules.Catalysts used are aluminum oxide or zeolites.

The residence time of the heavy oil in the pipeline is rather long (e.g.weeks, months) and the average speed of oil flow in pipelines is around5 miles/hour. Depending on the length of the pipelines, the oil beingtransport in pipelines can spend days flowing from start to end. Forexample, the proposed Keystone Pipeline, if completed, would be around2000 miles long. At 5 mile/hr, it will take 2-3 weeks for the oil toreach its destination. The residence time in the pipeline can be used toupgrade the heavy oil with the use of an appropriate catalyst. Theadvantages of this over the conventional means of upgrading heavy oil inrefineries are (i) faster refining time to end products since a part ofrefining the heavy oil is done before it gets to the refineries; (ii)increase in refinery capacity since it will take shorter time to createthe end products; (iii) less energy and cost necessary to upgrade heavyoil; (iv) lower temperature and less catalyst is used to do theupgrading since the available window for heavy oil upgrading reaction isdays/weeks instead of hours; (v) and less equipment such as reactors andheat exchangers is required for heavy oil upgrading in the refinerysince the pipeline serves as a reactor.

Preparation of Heavy Crude Oil in Water Emulsions

All emulsions samples were created using the following procedure unlessotherwise noted. The aqueous solution consisting of deionized water(DI), NaCl, an alkali, and a co-solvent is mixed and prepared. Allchemicals were measured and reported as weight percent of the aqueoussolution. A mixture of the aqueous solution and a heavy crude oil waspoured into a volumetric vial to create emulsions with differentconcentrations of oil (i.e., 20%, 40%, 60%, 80%, and 85%). Theconcentration of a crude oil in an emulsion is reported as a volumepercent of the total volume of an emulsion (w/v). The mixture was sealedand placed in a 100° C. oven. After reaching the oven temperature, thesample was hand shaken for 30 seconds every 20 minutes for an hour. Thesample was taken out of the oven and cooled down to a room temperatureof 25° C.±2° C. overnight.

Measurement of Apparent Viscosity of Emulsions

Apparent viscosities of all emulsion samples were measured using astainless steel tube viscometer unless otherwise stated.

Tube Viscometer

A stainless steel tubing was purchased from Swagelok with thespecifications listed in Table 4. A Rosemount 3051 Pressure Transmitterwas connected to the inlet and outlet of the tube viscometer using threeway fittings to record the differential pressure along the tube. Thetransmitter was calibrated and the range of measurable differentialpressure was set at 0-35 psi. 500D syringe pump from Teledyne Isco wasused to displace samples through the tube viscometer at constant flowrates. Viscosity standards (50, 100, 200, and 500 mPa s) were injectedthrough the tube to calibrate the tube viscometer based on differentialpressure readings, flow rates, and tube dimensions. An effective innerdiameter (ID) of 0.8176 mm was established after calibration. Emulsionsamples are injected into the tube viscometer at constant flow rates. Arange of flow rates were tested and pressure drops recorded to obtainapparent viscosity data at a range of apparent shear rates. When a flowrate was picked, the pressure drop across the tube was allowed to reachsteady state and recorded before the next flow rate was tested. After asample has been tested, the tube viscometer was cleaned thoroughly withthe following procedure. Flush out the emulsion from the tube with 0.1%NaCl brine. Clean out any residual crude oil present in the tube withtoluene. Displace all the toluene in the tube with 0.1% NaCl brine.

The Oil Content of the Emulsion has a Tremendous Effect on EmulsionViscosity.

The emulsion viscosity seems to be relatively insensitive to crude oilviscosity. The higher the crude oil viscosity, the greater the viscosityreduction of the oil when emulsified. For example, 80% emulsions for allfour oils show a viscosity range of 100-300 cP, while crude oilviscosities vary from 10,000-300,000 cP. Crude oil A shows 1500 timesreduction in viscosity while crude oil D shows only 40-50 timesreduction in viscosity when comparing 80% emulsions. All crude oils showevidence of yield stress except for crude oil C.

Amines are a type of co-solvents that can be used to make heavy oilemulsions. The biggest advantage of using an amine co-solvent is theproperty of amines to also act as an alkali to increase the pH. Withamine co-solvent, Applicants have eliminated the need to add alkali toincrease the pH, reducing chemicals used to just one chemical, the amineco-solvent. Applicants have tested numerous types of amines and foundthat diisopropylamine (DIPA) seems to have preferred properties. Amineco-solvents can also be ethoxylated to acquire the benefits shown inTable 5. FIG. 2 shows the results of using DIPA-15EO to prepare 85% oilA emulsions. There does not seem to be a clear trend with co-solventconcentration since multiple variables are changing at once (co-solventconcentration & pH). However, for up to 3% co-solvent, the viscosityseems to drop as co-solvent concentration increases.

FIG. 1 shows the extreme effect temperature can have on heavy crude oilviscosity. FIG. 3 is a test of 85% oil A emulsion viscosity at differenttemperature to observe the effect of temperature on emulsion viscosityusing an ARES rheometer. Increasing the temperature from 25-42° C. has abig effect on viscosity with further incremental change in temperatureproducing smaller benefits in terms of emulsion viscosity.

Emulsion stability is a very important variable for pipelinetransportation. Disastrous problems can arise if heavy crude oilseparates from the emulsion in the pipeline. Pipeline flow might have tobe stopped for days or weeks in case of problems. FIG. 4 shows emulsionviscosity measurements of same sample taken 7 days and 2.5 months afteremulsion preparation. Emulsion was stable after 2.5 months and no phaseseparation was observed. Surprisingly, Applicants observed that at lowshear rates, the emulsion tested possessed lower apparent viscosityafter 2.5 months compared to 7 days.

Applicants successfully created heavy crude oil emulsion by replacingmost of the water with a hydrophilic solvent, ethylene glycol. 3% w/wDIPA-15EO, 22% w/w DI, and 75% w/w ethylene glycol were mixed. 20% w/vof this stock solution was mixed with 80% w/v of oil C to make theemulsion in FIG. 11. For FIG. 11, the idea is that when heavy crude oilis produced from a well, it is produced as an emulsion with someproduced water emulsified within the oil. If 5% of the produced heavyoil emulsion is water, which is a reasonable assumption, 84.4% w/v (80%oil and 4.4% water) of this produced heavy oil emulsion can be combinedwith 0.6% DIPA-15EO and 15% ethylene glycol without any addition ofwater to create the emulsion.

Summary of Discoveries

Oil concentration increase equals higher emulsion viscosity equalshigher stability. Heavy oil viscosity seems to have very little effecton emulsion viscosity above 10,000 cp oil that was tested. Therefore,Applicants' emulsion making process has bigger effect when heavy oil isvery viscous. The composition of crude oil, especially the surfaceactive components that are activated with change in pH, seems to have alarge effect on emulsion viscosity. The composition of soap is differentfor every crude oil. The salinity of water increases the emulsionviscosity as salinity increases. The effect is minor compared to pHchange or oil %. Type of co-solvent used is important as illustrated inFIGS. 2, 9 and 10. Increasing co-solvent concentration decreases theemulsion viscosity up to a concentration and viscosity plateaus withincreasing concentration. The higher the number of EO, the morehydrophilic the soap/solvent system becomes and the higher the salinitytolerance (Table 5). Number of EO should depend on the salinity ofavailable water supply. Shear rate depends on pipeline diameter and flowrate. Generally, higher shear rate equals lower emulsion viscosity. Thetemperature of transport has significant effect on the emulsionviscosity. Higher temp results in lower emulsion viscosity and lowerstability (FIG. 3). Storage of emulsions doesn't seem to affect theemulsion negatively (FIG. 6). It even seems to lower the emulsionviscosity with time.

Comparison of heavy oil emulsion preparation methods have been madebetween Applicants' co-solvent method to established surfactant method(NPE). Applicants' results show significant advantages of the co-solventmethod compared to surfactant method (NPE). Applicants show emulsionviscosity data for higher oil content up to 90% oil. (FIG. 5, 6).Applicants have increased the emulsion viscosity data from 2 to 4different heavy oils (9,000-310,000 cP) demonstrating the versatility ofthe process. (Table 3). Applicants have shown that salinity requirementof the brine could be matched by optimizing the hydrophilicity (xEO) ofthe co-solvent. (Table 5). Applicants have shown the effect of salinityon the emulsion viscosity based on Applicants' ability to designemulsions that can tolerate higher salinity. A new type of amineco-solvents that also acts as an alkali has been tested and showedexcellent results with our 85% oil emulsions. (FIG. 2). The effect oftemperature on the heavy oil emulsion viscosity has been explored. (FIG.3). Applicants have tested viscosity of the same co-solvent emulsionsample 7 days and 2.5 months after preparation to show excellentstability of our emulsions. (FIG. 6).

V. Tables

TABLE 1 Summary of Apparent Viscosities of Micro-emulsion Formed withAmines Amine % of amine Capillary Viscosity (cP) TETA* 2 5.36 ± 0.55TETA* 1 9.98 ± 5.27 DMAPA** 2 2.71 ± 0.46 *TriethylenetetraAmine**Dimethylaminopropylamine

TABLE 2 Apparent Viscosities of micro- emulsion measured by capillarytube method Corrected apparent viscosity (cp) Shear Rate (s{circumflexover ( )}-1) 2% TETA 1% TETA 2% DMAPA 0.37 4 3 4 1.10 5 4 3 3.65 5 6 310.95 5 8 3 18.26 5 9 3 36.51 6 10 3 54.77 6 12 2 91.28 6 13 2 182.57 616 2 365.13 6 19 2 AVG 5.4 10.0 2.7 STDEV 0.6 5.3 0.5

TABLE 3 Heavy crude oil properties TotalC (A) Zuata (B) PRB (C) Ugnu (D)Origins Unknown Venezuela Canada Alaska Dynamic viscosity (cP) at310,000 93,000 62,500 9,000 25° C. & 10 s⁻¹ Specific gravity at 25° C. ?? ? ? Total acid number (mg ? ? ? ? KOH/g oil)

TABLE 4 Tube viscometer specifications Tube dimensions Outer diameter(OD) 1.5875 mm Wall thickness 0.4064 mm Inner diameter (ID) 0.7747 mmLength 92.964 cm

TABLE 5 Emulsion: Oil A (60% w/v) 1.6% aq. Ph—xEO 0.2% aq. NaOH Type ofco-solvent 0.1% NaCl 0.8% NaCl 1.6% NaCl 2.4% NaCl No co-solvent FluidSolid Solid Solid Ph—2EO Fluid Solid Solid Solid Ph—8EO Fluid FluidFluid Solid Ph—16EO Fluid Fluid Fluid Solid Ph—20EO Fluid Fluid FluidSolid

*Fluid describes O/W emulsions that are single phase, homogeneous, andfluid enough to measure viscosity

*Solid describes emulsions that consist of multiple phases, areextremely heterogeneous, or too viscous to measure viscosity.

TABLE 6 Effect of many variables on emulsion viscosity and stabilityViscosity Stability Heavy Crude Oil Oil %¹ ↑ ↑ ↑ Viscosity² ↑ minoreffect ? Composition³ Aqueous Salinity⁴ ↑ ↑ ? Alkali Conc.^(5a) NaOH ↑ ↑↑ Na2CO3^(5b) ↑ ↑ ↑ Co-solvent Type⁶ Concentration⁷ ↑ ↓ ? # of EO's⁸ ↑Minor effect ? Shear rate in ↑ ↓ ? pipeline⁹ Environmental Temp of ↑ ↓ ↓Transport¹⁰ Time of ↑ ↓ Heavy Crude Oil storage¹¹ Emulsion PrepProcedure Temp of ↑ ↓ ↑ mixing¹² Mixing timer¹² ↑ ↑ ↑ Mixing ↑ ↑ ↑speed¹²

VI. Embodiments Embodiment 1

A heavy crude oil emulsion comprising a heavy crude oil, water and aco-solvent, wherein said co-solvent is an alkylamine or a compoundhaving the formula:

wherein R^(1A) and R^(1B) are independently hydrogen, unsubstitutedC₁-C₈ alkyl, unsubstituted cycloalkyl, unsubstituted heterocycloalkyl,unsubstituted aryl, unsubstituted heteroaryl, C₁-C₆ alkylamine or

R² and R³ are independently hydrogen or unsubstituted C₁-C₂ alkyl; n isan integer from 1 to 30; m is an integer from 1 to 30; and wherein saidheavy crude oil emulsion is within a transport vessel.

Embodiment 2

The heavy crude oil emulsion of embodiment 1, wherein R^(1A) and R^(1B)are independently unsubstituted C₁-C₆ alkyl.

Embodiment 3

The heavy crude oil emulsion of any one of the preceding embodiments,wherein the number of total carbon atoms within R^(1A) and R^(1B)combined does not exceed 8.

Embodiment 4

The heavy crude oil emulsion of any one of the preceding embodiments,wherein R^(1A) and R^(1B) are independently unsubstituted C₁-C₄ alkyl.

Embodiment 5

The heavy crude oil emulsion of any one of the preceding embodiments,wherein R^(1A) and R^(1B) are unsubstituted isopropyl.

Embodiment 6

The heavy crude oil emulsion of one of embodiments 1 to 5, wherein n isan integer from 1 to 10.

Embodiment 7

The heavy crude oil emulsion of one of embodiments 1 to 5, wherein n isan integer from 1 to 6.

Embodiment 8

The heavy crude oil emulsion of one of embodiments 1 to 5, wherein R² ishydrogen and n is 1 to 3.

Embodiment 9

The heavy crude oil emulsion of any one of the preceding embodiments,wherein m is an integer from 1 to 10.

Embodiment 10

The heavy crude oil emulsion of any one of the preceding embodiments,wherein m is 1 to 6.

Embodiment 11

The heavy crude oil emulsion of any one of the preceding embodiments,wherein R³ is hydrogen and m is 1 to 3.

Embodiment 12

The heavy crude oil emulsion of any one of the preceding embodiments,wherein R^(1A) and R^(1B) are independently hydrogen or C₂-C₆alkylamine.

Embodiment 13

The heavy crude oil emulsion of any one of the preceding embodiments,wherein R^(1A) is hydrogen and R^(1B) is C₄-C₆ alkylamine.

Embodiment 14

The heavy crude oil emulsion of any one of the preceding embodiments,wherein R^(1A) and R^(1B) are independently C₂-C₄ alkylamine.

Embodiment 15

The heavy crude oil emulsion of one of embodiments 12 to 14, whereinsaid alkylamine is an alkylpolyamine.

Embodiment 16

The heavy crude oil emulsion of any one of the preceding embodiments,wherein R^(1A) is hydrogen and R^(1B) is unsubstituted cycloalkyl.

Embodiment 17

The heavy crude oil emulsion of any one of the preceding embodiments,wherein R^(1B) is 6 membered cycloalkyl.

Embodiment 18

The heavy crude oil emulsion of any one of the preceding embodiments,wherein R^(1A) is hydrogen and R^(1B) is unsubstituted aryl.

Embodiment 19

The heavy crude oil emulsion of any one of the preceding embodiments,wherein R^(1B) is phenyl.

Embodiment 20

The heavy crude oil emulsion of embodiment 1, wherein said compound hasthe formula:

wherein R² is methyl or ethyl; o is an integer from 0 to 15; and p is aninteger from 1 to 10.

Embodiment 21

The heavy crude oil emulsion of embodiment 20, wherein R² is hydrogen, ois 0 and p is 1 to 6.

Embodiment 22

The heavy crude oil emulsion of embodiment 1, wherein said compound hasthe formula:

wherein R² is ethyl; q is an integer from 0 to 10; r is an integer from0 to 10; and s is an integer from 1 to 10.

Embodiment 23

The heavy crude oil emulsion of embodiment 1, wherein said alkylamine isdiisopropylamine.

Embodiment 24

The heavy crude oil emulsion of embodiment 1, wherein said alkylamine isan alkylpolyamine.

Embodiment 25

The heavy crude oil emulsion of embodiment 24, wherein saidalkylpolyamine is dimethylaminopropylamine, triethylenetetramine ordiethylenetriamine.

Embodiment 26

The heavy crude oil emulsion as in one of embodiments 1 to 25, whereinsaid co-solvent is present from about 0.01% to about 5% (w/v).

Embodiment 27

The heavy crude oil emulsion as in one of embodiments 1 to 26, furthercomprising a compound of formula:

wherein L¹ is unsubstituted C₁-C₆ alkylene, unsubstituted phenylene,unsubstituted cyclohexylene, unsubstituted cyclopentylene ormethyl-substituted cyclopentylene; R² is independently hydrogen, methylor ethyl;R³ is independently hydrogen or

R⁴ is independently hydrogen, methyl or i ethyl; n is an integer from 0to 30, and m is an integer from 0 to 30.

Embodiment 28

The heavy crude oil emulsion as in one of embodiments 1 to 26, furthercomprising a compound of formula:

wherein R¹ is independently hydrogen, unsubstituted C₁-C₆ alkyl orR⁵—OH; R² is independently hydrogen or unsubstituted C₁-C₂ alkyl; R⁵ isindependently a bond or unsubstituted C₁-C₆ alkyl; n is an integer from1 to 30; o is an integer from 1 to 5; and z is an integer from 1 to 5.

Embodiment 29

The heavy crude oil emulsion of embodiment 27 or 28, wherein saidcompound is present at about 0.01% w/v to about 5% w/v.

Embodiment 30

The heavy crude oil emulsion of any one of the preceding embodiments,wherein the heavy crude oil is present from about 10% to about 90%(w/v).

Embodiment 31

The heavy crude oil emulsion of any one of the preceding embodiments,further comprising a surfactant.

Embodiment 32

The heavy crude oil emulsion of any one of the preceding embodiments,further comprising an alkali agent.

Embodiment 33

The heavy crude oil emulsion of embodiment 32, wherein said alkali agentis NaOH, KOH, LiOH, Na₂CO₃, NaHCO₃, Na-metaborate, Na silicate, Naorthosilicate, Na acetate or NH₄OH.

Embodiment 34

The heavy crude oil emulsion of embodiment 32, wherein said alkali agentis present from about 0.01% to about 3% (w/v).

Embodiment 35

The heavy crude oil emulsion of any one of the preceding embodiments,further comprising a salt.

Embodiment 36

The heavy crude oil emulsion of embodiment 35, wherein said salt isNaCl, Na₂SO₄, K₂SO₄ or KCl.

Embodiment 37

The heavy crude oil emulsion of embodiment 35, wherein said salt ispresent in an amount sufficient to increase the solubility of saidco-solvent in said emulsion relative to the absence of said salt.

Embodiment 38

The heavy crude oil emulsion of embodiment 35, wherein said salt ispresent from about 0.01% to about 4% (w/v).

Embodiment 39

The heavy crude oil emulsion of any one of the preceding embodiments,further comprising a catalyst.

Embodiment 40

The heavy crude oil emulsion of any one of the preceding embodiments,wherein said emulsion is at a transport temperature.

Embodiment 41

The heavy crude oil emulsion of embodiment 40, wherein said transporttemperature is less than 60° C.

Embodiment 42

The heavy crude oil emulsion of any one of the preceding embodiments,wherein said heavy crude oil is present from about 10% to about 90%(w/v).

Embodiment 43

The heavy crude oil emulsion of any one of the preceding embodiments,wherein said viscosity of said heavy crude oil is about 100,000 cP atambient temperature.

Embodiment 44

The heavy crude oil emulsion of any one of the preceding embodiments,wherein said viscosity of said heavy crude oil is about 200,000 cP atambient temperature.

Embodiment 45

The heavy crude oil emulsion of any one of the preceding embodiments,wherein said viscosity of said heavy crude oil is about 300,000 cP atambient temperature.

Embodiment 46

The heavy crude oil emulsion of any one of the preceding embodiments,wherein said viscosity of said emulsion is about a 1,000 times less thanthe viscosity of said heavy crude oil.

Embodiment 47

The heavy crude oil emulsion of any one of the preceding embodiments,wherein said viscosity of said emulsion is about a 10,000 times lessthan the viscosity of said heavy crude oil.

Embodiment 48

The heavy crude oil emulsion of any one of the preceding embodiments,wherein said viscosity of said emulsion is about a 100,000 times lessthan the viscosity of said heavy crude oil.

Embodiment 49

The heavy crude oil emulsion of any one of the preceding embodiments,wherein said transport vessel is a pipeline.

Embodiment 50

The heavy crude oil emulsion of any one of the preceding embodiments,wherein said transport vessel forms part of a transportation vehicle.

Embodiment 51

The heavy crude oil emulsion as in one of embodiments 1-49, wherein saidemulsion is transported in a pipeline.

Embodiment 52

The heavy crude oil emulsion of any one of the preceding embodiments,wherein said emulsion is stable at ambient temperature for at least anhour.

Embodiment 53

The heavy crude oil emulsion of any one of the preceding embodiments,wherein said emulsion is stable at ambient temperature for at least aday.

Embodiment 54

The heavy crude oil emulsion of any one of the preceding embodiments,wherein said emulsion is stable at ambient temperature for at least aweek.

Embodiment 55

The heavy crude oil emulsion of any one of the preceding embodiments,wherein said emulsion is stable at ambient temperature for at least amonth.

Embodiment 56

The heavy crude oil emulsion of embodiment 54 or 55, wherein saidambient temperature is less than 80° C.

Embodiment 57

The heavy crude oil emulsion of embodiment 54 or 55, wherein saidambient temperature is less than 60° C.

Embodiment 58

The heavy crude oil emulsion of embodiment 54 or 55, wherein saidambient temperature is less than 40° C.

Embodiment 59

A method of forming a heavy crude oil emulsion, said method comprising:(i) contacting a heavy crude oil extracted from an oil reservoir with aco-solvent and water at an emulsion forming temperature, thereby forminga high temperature heavy crude oil emulsion; (ii) allowing said hightemperature heavy crude oil emulsion to cool to a transport temperature,thereby forming a heavy crude oil emulsion; wherein said co-solvent isan alkylamine or a compound having the formula:

wherein R^(1A) and R^(1B) are independently hydrogen, unsubstitutedC₁-C₈ alkyl, unsubstituted cycloalkyl, unsubstituted heterocycloalkyl,unsubstituted aryl, unsubstituted heteroaryl, C₁-C₆ alkylamine or

R² and R³ are independently hydrogen or unsubstituted C₁-C₂ alkyl; n isan integer from 1 to 30; and m is an integer from 1 to 30.

Embodiment 60

The method of embodiment 59, wherein R^(1A) and R^(1B) are independentlyunsubstituted C₁-C₆ alkyl.

Embodiment 61

The method of embodiment 59 or 60, wherein the number of total carbonatoms within R^(1A) and R^(1B) combined does not exceed 8.

Embodiment 62

The method of any one of embodiments 59-61, wherein R^(1A) and R^(1B)are independently unsubstituted C₁-C₄ alkyl.

Embodiment 63

The method of any one of embodiments 59-62, wherein R^(1A) and R^(1B)are unsubstituted isopropyl.

Embodiment 64

The method of one of embodiments 59 to 63, wherein n is an integer from1 to 10.

Embodiment 65

The method of one of embodiments 59 to 53, wherein n is an integer from1 to 6.

Embodiment 66

The method of one of embodiments 59 to 63, wherein R² is hydrogen and nis 1 to 3.

Embodiment 67

The method of embodiment 59, wherein said compound has the formula:

wherein R² is methyl or ethyl; o is an integer from 0 to 15; and p is aninteger from 1 to 10.

Embodiment 68

The method of embodiment 67, wherein R² is hydrogen, o is 0 and p is 1to 6.

Embodiment 69

The method of embodiment 59, wherein said compound has the formula:

wherein R² is ethyl; q is an integer from 0 to 10; r is an integer from0 to 10; and s is an integer from 1 to 10.

Embodiment 70

The method of embodiment 59, wherein said alkylamine isdiisopropylamine.

Embodiment 71

The method of embodiment 59, wherein said alkylamine is analkylpolyamine.

Embodiment 72

The method of embodiment 71, wherein said alkylpolyamine isdimethylaminopropylamine, triethylenetetramine or diethylenetriamine.

Embodiment 73

The method of any one of embodiments 59-72, further comprisingcontacting said heavy crude oil extracted from an oil reservoir with acompound of formula:

wherein L¹ is unsubstituted C₁-C₆ alkylene, unsubstituted phenylene,unsubstituted cyclohexylene, unsubstituted cyclopentylene ormethyl-substituted cyclopentylene; R² is independently hydrogen, methylor ethyl; R³ is independently hydrogen or

R⁴ is independently hydrogen, methyl or ethyl; n is an integer from 0 to30, and m is an integer from 0 to 30.

Embodiment 74

The method of any one of embodiments 59-73, further comprisingcontacting said heavy crude oil extracted from an oil reservoir with acompound of formula:

wherein R¹ is independently hydrogen, unsubstituted C₁-C₆ alkyl orR⁵—OH; R² is independently hydrogen or unsubstituted C₁-C₂ alkyl; R⁵ isindependently a bond or unsubstituted C₁-C₆ alkyl; n is an integer from1 to 30; o is an integer from 1 to 5; and z is an integer from 1 to 5.

Embodiment 75

The method of embodiment 73 or 74, wherein said compound is present fromabout 0.01% to about 5% (w/v).

Embodiment 76

The method of embodiment 59 to 75, wherein said co-solvent is presentfrom about 0.01% to about 5% (w/v).

Embodiment 77

The method of any one of embodiments 59-76, wherein said heavy crude oilis present from about 10% to about 95% (w/v).

Embodiment 78

The method of any one of embodiments 59-77, further comprisingcontacting said heavy crude oil extracted from an oil reservoir with analkali agent.

Embodiment 79

The method of any one of embodiments 59-78, further comprisingcontacting said heavy crude oil extracted from an oil reservoir with acatalyst.

Embodiment 80

A method of optimizing a heavy crude oil emulsion, said methodcomprising: (i) contacting a plurality of heavy crude oil samplesextracted from an oil reservoir with an amount of a co-solvent, anamount of a salt and an amount of water at an emulsion formingtemperature, wherein said amount of a co-solvent, the amount of a saltand said amount of water is different for each of said plurality ofheavy crude oil samples, thereby forming a plurality of different hightemperature heavy crude oil emulsion samples; (ii) allowing saidplurality of different high temperature heavy crude oil emulsion samplesto cool to an ambient temperature, thereby forming a plurality ofdifferent low temperature heavy crude oil emulsion samples; (iii)identifying a low temperature heavy crude oil emulsion sample amongstsaid plurality of different low temperature heavy crude oil emulsionsamples having a viscosity at least 100 times lower than the viscosityof said heavy crude oil, thereby optimizing a heavy crude oil emulsion;wherein said co-solvent is an alkylamine or a compound having theformula:

wherein R^(1A) and R^(1B) are independently hydrogen, unsubstitutedC₁-C₈ alkyl, unsubstituted cycloalkyl, unsubstituted heterocycloalkyl,unsubstituted aryl, unsubstituted heteroaryl, C₁-C₆ alkylamine or

R² and R³ are independently hydrogen or unsubstituted C₁-C₂ alkyl; n isan integer from 1 to 30; and m is an integer from 1 to 30.

Embodiment 81

The method of embodiment 80, wherein said co-solvent is present fromabout 0.01% to about 5% (w/v).

Embodiment 82

The method of embodiment 80, wherein said heavy crude oil is presentfrom about 10% to about 95% (w/v).

Embodiment 83

A method of transporting a heavy crude oil, comprising: (i) extracting aheavy crude oil from an oil reservoir, thereby forming an extractedheavy crude oil; (ii) contacting said extracted heavy crude oil with aco-solvent and water at an emulsion forming temperature, thereby forminga high temperature heavy crude oil emulsion; (iii) allowing said hightemperature heavy crude oil emulsion to cool to a transport temperature,thereby forming a heavy crude oil emulsion; (iv) transporting said heavycrude oil emulsion from a first location to a second location, therebytransporting said heavy crude oil; wherein said co-solvent is analkylamine or a compound having the formula:

wherein R^(1A) and R^(1B) are independently hydrogen, unsubstitutedC₁-C₈ alkyl, unsubstituted cycloalkyl, unsubstituted heterocycloalkyl,unsubstituted aryl, unsubstituted heteroaryl, C₁-C₆ alkylamine or

R² and R³ are independently hydrogen or unsubstituted C₁-C₂ alkyl;n is an integer from 1 to 30; and m is an integer from 1 to 30.

Embodiment 84

The method of embodiment 83, wherein said first location is a productionwell.

Embodiment 85

The method of embodiment 83, further comprising contacting saidextracted heavy crude oil with a catalyst.

Embodiment 86

The method of embodiment 83 or 85, wherein said transporting of step(iv) is performed in a vessel.

Embodiment 87

The method of embodiment 86, wherein said vessel is a pipeline.

Embodiment 88

The method of embodiment 87, wherein said vessel forms part of atransportation vehicle.

Embodiment 89

The method of embodiment 85, further comprising after said transportingof step (iv) separating said heavy crude oil from said co-solvent andsaid water, thereby forming a recovered heavy crude oil.

Embodiment 90

A method of forming a heavy crude oil emulsion in a production well,said method comprising contacting an extracted heavy crude oil in aproduction well with a co-solvent and water, thereby forming a heavycrude oil emulsion in the production well, wherein said co-solvent is analkylamine or a compound having the formula:

wherein R^(1A) and R^(1B) are independently hydrogen, unsubstitutedC₁-C₈ alkyl, unsubstituted cycloalkyl, unsubstituted heterocycloalkyl,unsubstituted aryl, unsubstituted heteroaryl, C₁-C₆ alkylamine or

R² and R³ are independently hydrogen or unsubstituted C₁-C₂ alkyl;n is an integer from 1 to 30; and m is an integer from 1 to 30.

Embodiment 91

The method of embodiment 90, wherein said extracted heavy crude oil ispresent from about 10% to about 95% (w/v).

Embodiment 92

The method of embodiment 90, wherein said alkylamine isdiisopropylamine.

Embodiment 93

The method of embodiment 90, wherein said alkylamine is analkylpolyamine.

Embodiment 94

The method of embodiment 93, wherein said alkylpolyamine isdimethylaminopropylamine, triethylenetetramine or diethylenetriamine.

Embodiment 95

The method of any one of embodiments 90-94, wherein said extracted heavycrude oil has a viscosity of at least 100,000 cP.

Embodiment 96

The method of any one of embodiments 90-95, wherein said extracted heavycrude oil has a viscosity of at least 200,000 cP.

Embodiment 97

The method of any one of embodiments 90-96, wherein said extracted heavycrude oil has a viscosity of at least 300,000 cP.

Embodiment 98

The method of any one of embodiments 90-97, wherein said extracted heavycrude oil has a viscosity of at least 1,000,000 cP.

Embodiment 99

The method of any one of embodiments 90-98, wherein the viscosity ofsaid heavy crude oil emulsion is 1,000 times lower than the viscosity ofsaid extracted heavy crude oil.

Embodiment 100

The method of any one of embodiments 90-99, wherein the viscosity ofsaid heavy crude oil emulsion is 10,000 times lower than the viscosityof said extracted heavy crude oil.

Embodiment 101

The method of any one of embodiments 90-101, wherein the viscosity ofsaid heavy crude oil emulsion is 100,000 times lower than the viscosityof said extracted heavy crude oil.

Embodiment 102

The method of any one of embodiments 90-101, further comprisingcontacting said extracted heavy crude oil with a compound of formula:

wherein L¹ is unsubstituted C₁-C₆ alkylene, unsubstituted phenylene,unsubstituted cyclohexylene, unsubstituted cyclopentylene ormethyl-substituted cyclopentylene; R² is independently hydrogen, methylor ethyl; R³ is independently hydrogen or

R⁴ is independently hydrogen, methyl or ethyl; n is an integer from 0 to30, and m is an integer from 0 to 30.

Embodiment 103

The method of any one of embodiments 90-102, further comprisingcontacting said extracted heavy crude oil with a compound of formula:

wherein R¹ is independently hydrogen, unsubstituted C₁-C₆ alkyl orR⁵—OH; R² is independently hydrogen or unsubstituted C₁-C₂ alkyl; R⁵ isindependently a bond or unsubstituted C₁-C₆ alkyl; n is an integer from1 to 30; o is an integer from 1 to 5; and z is an integer from 1 to 5.

Embodiment 104

The method of any one of embodiments 90-103, further comprisingcontacting said extracted heavy crude oil with a surfactant.

Embodiment 105

The method of any one of embodiments 90-104, further comprisingcontacting said extracted heavy crude oil with a catalyst.

Embodiment 106

A method of transporting an extracted heavy crude oil from a productionwell, comprising: (i) contacting an extracted heavy crude oil in aproduction well with a co-solvent, and water at an emulsion formingtemperature, thereby forming a heavy crude oil emulsion in a productionwell; (ii) transporting said heavy crude oil emulsion from saidproduction well to the surface, thereby transporting said extractedheavy crude oil from said production well, wherein said co-solvent is analkylamine or a compound having the formula:

wherein R^(1A) and R^(1B) are independently hydrogen, unsubstitutedC₁-C₈ alkyl, unsubstituted cycloalkyl, unsubstituted heterocycloalkyl,unsubstituted aryl, unsubstituted heteroaryl, C₁-C₆ alkylamine or

R² and R³ are independently hydrogen or unsubstituted C₁-C₂ alkyl; n isan integer from 1 to 30; and m is an integer from 1 to 30.

Embodiment 107

The method of embodiment 106, wherein said transporting of step (ii)further comprises moving said heavy crude oil transport emulsion with amechanical pump.

Embodiment 108

The method of embodiment 107, wherein said mechanical pump is anelectrical submersible pump.

Embodiment 109

A heavy crude oil emulsion comprising an amphiphilic co-solvent, a firstphase and a second phase, wherein said first phase comprises anoil-immiscible compound and said second phase comprises a heavy crudeoil; wherein said amphiphilic co-solvent is an alkylamine or a compoundhaving the formula:

wherein R^(1A) and R^(1B) are independently hydrogen, unsubstitutedC₁-C₈ alkyl, unsubstituted cycloalkyl, unsubstituted heterocycloalkyl,unsubstituted aryl, unsubstituted heteroaryl, C₁-C₆ alkylamine or

R² and R³ are independently hydrogen or unsubstituted C₁-C₂ alkyl; n isan integer from 1 to 30; and m is an integer from 1 to 30.

Embodiment 110

The heavy crude oil emulsion of embodiment 109, wherein said heavy crudeoil emulsion does not comprise water.

Embodiment 111

The heavy crude oil emulsion of embodiment 109, wherein said heavy crudeoil emulsion further comprises heavy crude oil water.

Embodiment 112

The heavy crude oil emulsion of embodiment 111, wherein the amount ofwater in said heavy crude oil emulsion is equal to the amount of saidheavy crude oil water.

Embodiment 113

The heavy crude oil emulsion of embodiment 111, wherein the amount ofsaid heavy crude oil water is less than about 20% (w/v).

Embodiment 114

The heavy crude oil emulsion of embodiment 111, wherein the amount ofsaid heavy crude oil water is less than about 2% (w/v).

Embodiment 115

The heavy crude oil emulsion of embodiment 111, wherein the amount ofsaid heavy crude oil water is less than about 1% (w/v).

Embodiment 116

The heavy crude oil emulsion of embodiment 109, wherein said amphiphilicco-solvent is present in said first phase and said second phase.

Embodiment 117

The heavy crude oil emulsion of embodiment 109, wherein said first phaseis about 80% oil-immiscible compound.

Embodiment 118

The heavy crude oil emulsion of embodiment 109, wherein said first phaseis about 95% oil-immiscible compound.

Embodiment 119

The heavy crude oil emulsion of embodiment 109, wherein said first phaseis about 100% oil-immiscible compound.

Embodiment 120

The heavy crude oil emulsion of embodiment 109, wherein saidoil-immiscible compound is ethylene glycol, di-ethylene glycol,propylene glycol, pentaerythritol, sorbitol or methanol.

Embodiment 121

The heavy crude oil emulsion of embodiment 109, further comprising asurfactant.

Embodiment 122

The heavy crude oil emulsion of embodiment 109, wherein the viscosity ofsaid heavy crude oil emulsion is lower than the viscosity of said heavycrude oil.

Embodiment 123

The heavy crude oil emulsion of embodiment 109, wherein the emulsion isformed at an ambient temperature.

Embodiment 124

A method of forming a heavy crude oil emulsion, said method comprising:(i) contacting a heavy crude oil extracted from an oil reservoir with anoil-immiscible compound and an amphiphilic co-solvent at an emulsionforming temperature, thereby forming a high temperature heavy crude oilemulsion; (ii) allowing said high temperature heavy crude oil emulsionto cool to a transport temperature, thereby forming a heavy crude oilemulsion; wherein said amphiphilic co-solvent is an alkylamine or acompound having the formula:

wherein R^(1A) and R^(1B) are independently hydrogen, unsubstitutedC₁-C₈ alkyl, unsubstituted cycloalkyl, unsubstituted heterocycloalkyl,unsubstituted aryl, unsubstituted heteroaryl, C₁-C₆ alkylamine or

R² and R³ are independently hydrogen or unsubstituted C₁-C₂ alkyl; n isan integer from 1 to 30; and m is an integer from 1 to 30.

Embodiment 125

The method of embodiment 124, wherein said extracted heavy crude oilemulsion further comprises heavy crude oil water.

Embodiment 126

The method of embodiment 125, wherein the amount of water in said heavycrude oil emulsion is equal to the amount of said heavy crude oil water.

Embodiment 127

The method of embodiment 124, further comprising contacting said heavycrude oil extracted from an oil reservoir with a surfactant.

Embodiment 128

The method of embodiment 124, wherein said oil-immiscible compound isethylene glycol, di-ethylene glycol, propylene glycol, pentaerythritol,sorbitol or methanol.

Embodiment 129

A method of forming a heavy crude oil emulsion in a production well,said method comprising contacting an extracted heavy crude oil in aproduction well with an oil-immiscible compound and an amphiphilicco-solvent, thereby forming a heavy crude oil emulsion in a productionwell; wherein said amphiphilic co-solvent is an alkylamine or a compoundhaving the formula:

wherein R^(1A) and R^(1B) are independently hydrogen, unsubstitutedC₁-C₈ alkyl, unsubstituted cycloalkyl, unsubstituted heterocycloalkyl,unsubstituted aryl, unsubstituted heteroaryl, C₁-C₆ alkylamine or

R² and R³ are independently hydrogen or unsubstituted C₁-C₂ alkyl; n isan integer from 1 to 30; and m is an integer from 1 to 30.

Embodiment 130

The method of embodiment 129, wherein said extracted heavy crude oilemulsion further comprises heavy crude oil water.

Embodiment 131

The method of embodiment 130, wherein the amount of water in said heavycrude oil emulsion is equal to the amount of said heavy crude oil water.

Embodiment 132

The method of embodiment 130, further comprising contacting saidextracted heavy crude oil with a surfactant.

Embodiment 133

The method of embodiment 129, wherein said oil-immiscible compound isethylene glycol, di-ethylene glycol, propylene glycol, pentaerythritol,sorbitol or methanol.

Embodiment 134

A method of transporting an extracted heavy crude oil from a productionwell, comprising: (i) contacting an extracted heavy crude oil in aproduction well with an oil-immiscible compound, and an amphiphilicco-solvent at an emulsion forming temperature, thereby forming a heavycrude oil emulsion in a production well; (ii) transporting said heavycrude oil emulsion from said production well to the surface, therebytransporting said extracted heavy crude oil from said production well;wherein said amphiphilic co-solvent is an alkylamine or a compoundhaving the formula:

wherein R^(1A) and R^(1B) are independently hydrogen, unsubstitutedC₁-C₈ alkyl, unsubstituted cycloalkyl, unsubstituted heterocycloalkyl,unsubstituted aryl, unsubstituted heteroaryl, C₁-C₆ alkylamine or

R² and R³ are independently hydrogen or unsubstituted C₁-C₂ alkyl; n isan integer from 1 to 30; and m is an integer from 1 to 30.

Embodiment 135

The method of embodiment 134, wherein said extracted heavy crude oilemulsion further comprises heavy crude oil water.

Embodiment 136

The method of embodiment 135, wherein the amount of water in said heavycrude oil emulsion is equal to the amount of said heavy crude oil water.

Embodiment 137

The method of embodiment 134, further comprising contacting saidextracted heavy crude oil with a surfactant.

Embodiment 138

The method of embodiment 134, wherein said oil-immiscible compound isethylene glycol, di-ethylene glycol, propylene glycol, pentaerythritol,sorbitol or methanol.

Embodiment 139

A non-aqueous composition comprising an oil-immiscible compound, and anamphiphilic co-solvent, wherein said amphiphilic co-solvent is analkylamine or a compound having the formula:

wherein R^(1A) and R^(1B) are independently hydrogen, unsubstitutedC₁-C₈ alkyl, unsubstituted cycloalkyl, unsubstituted heterocycloalkyl,unsubstituted aryl, unsubstituted heteroaryl, C₁-C₆ alkylamine or

R² and R³ are independently hydrogen or unsubstituted C₁-C₂ alkyl; n isan integer from 1 to 30; and m is an integer from 1 to 30.

Embodiment 140

The non-aqueous composition of embodiment 139, wherein saidoil-immiscible compound is ethylene glycol, di-ethylene glycol,propylene glycol, pentaerythritol, sorbitol or methanol.

Embodiment 141

The non-aqueous composition of embodiment 139, further comprising asurfactant.

What is claimed is:
 1. A heavy crude oil emulsion comprising a heavycrude oil, water and a co-solvent, wherein said co-solvent is analkylamine or a compound having the formula:

wherein R^(1A) and R^(1B) are independently hydrogen, unsubstitutedC₁-C₈ alkyl, unsubstituted cycloalkyl, unsubstituted heterocycloalkyl,unsubstituted aryl, unsubstituted heteroaryl, C₁-C₆ alkylamine or

R² and R³ are independently hydrogen or unsubstituted C₁-C₂ alkyl; n isan integer from 1 to 30; m is an integer from 1 to 30; and wherein saidheavy crude oil emulsion is within a transport vessel.
 2. The heavycrude oil emulsion of claim 1, wherein R^(1A) and R^(1B) areindependently unsubstituted C₁-C₆ alkyl.
 3. The heavy crude oil emulsionof one of claims 1, wherein n is an integer from 1 to
 10. 4. The heavycrude oil emulsion of claim 1, wherein m is 1 to
 6. 5. The heavy crudeoil emulsion of claim 1, wherein R^(1A) and R^(1B) are independentlyhydrogen or C₂-C₆ alkylamine.
 6. The heavy crude oil emulsion of claim5, wherein R^(1A) is hydrogen and R^(1B) is C₄-C₆ alkylamine.
 7. Theheavy crude oil emulsion of claim 1, wherein said alkylamine is analkylpolyamine.
 8. The heavy crude oil emulsion of claim 1, wherein saidcompound has the formula:

wherein R² is methyl or ethyl; o is an integer from 0 to 15; and p is aninteger from 1 to
 10. 9. The heavy crude oil emulsion of claim 1,wherein said heavy crude oil is an asphaltene.
 10. The heavy crude oilemulsion of claim 1, further comprising a surfactant.
 11. The heavycrude oil emulsion of claim 1, further comprising an alkali agent. 12.The heavy crude oil emulsion of claim 1, further comprising a salt. 13.The heavy crude oil emulsion of claim 1, wherein said emulsion is at atransport temperature.
 14. A method of forming a heavy crude oilemulsion, said method comprising: (i) contacting a heavy crude oilextracted from an oil reservoir with a co-solvent and water at anemulsion forming temperature, thereby forming a high temperature heavycrude oil emulsion; (ii) allowing said high temperature heavy crude oilemulsion to cool to a transport temperature, thereby forming a heavycrude oil emulsion; wherein said co-solvent is an alkylamine or acompound having the formula:

wherein R^(1A) and R^(1B) are independently hydrogen, unsubstitutedC₁-C₈ alkyl, unsubstituted cycloalkyl, unsubstituted heterocycloalkyl,unsubstituted aryl, unsubstituted heteroaryl, C₁-C₆ alkylamine or

R² and R³ are independently hydrogen or unsubstituted C₁-C₂ alkyl; n isan integer from 1 to 30; and m is an integer from 1 to
 30. 15. A methodof transporting a heavy crude oil, comprising: (i) extracting a heavycrude oil from an oil reservoir, thereby forming an extracted heavycrude oil; (ii) contacting said extracted heavy crude oil with aco-solvent and water at an emulsion forming temperature, thereby forminga high temperature heavy crude oil emulsion; (iii) allowing said hightemperature heavy crude oil emulsion to cool to a transport temperature,thereby forming a heavy crude oil emulsion; (iv) transporting said heavycrude oil emulsion from a first location to a second location, therebytransporting said heavy crude oil; wherein said co-solvent is analkylamine or a compound having the formula:

wherein R^(1A) and R^(1B) are independently hydrogen, unsubstitutedC₁-C₈ alkyl, unsubstituted cycloalkyl, unsubstituted heterocycloalkyl,unsubstituted aryl, unsubstituted heteroaryl, C₁-C₆ alkylamine or

R² and R³ are independently hydrogen or unsubstituted C₁-C₂ alkyl; n isan integer from 1 to 30; and m is an integer from 1 to
 30. 16. Themethod of claim 15, wherein said first location is a production well.17. The method of claim 15, wherein said transporting of step (iv) isperformed in a vessel.
 18. The method of claim 17, wherein said vesselis a pipeline.
 19. A method of forming a heavy crude oil emulsion in aproduction well, said method comprising contacting an extracted heavycrude oil in a production well with a co-solvent and water, therebyforming a heavy crude oil emulsion in the production well, wherein saidco-solvent is an alkylamine or a compound having the formula:

wherein R^(1A) and R^(1B) are independently hydrogen, unsubstitutedC₁-C₈ alkyl, unsubstituted cycloalkyl, unsubstituted heterocycloalkyl,unsubstituted aryl, unsubstituted heteroaryl, C₁-C₆ alkylamine or

R² and R³ are independently hydrogen or unsubstituted C₁-C₂ alkyl; n isan integer from 1 to 30; and m is an integer from 1 to
 30. 20. A methodof transporting an extracted heavy crude oil from a production well,comprising: (i) contacting an extracted heavy crude oil in a productionwell with a co-solvent, and water at an emulsion forming temperature,thereby forming a heavy crude oil emulsion in a production well; (ii)transporting said heavy crude oil emulsion from said production well tothe surface, thereby transporting said extracted heavy crude oil fromsaid production well, wherein said co-solvent is an alkylamine or acompound having the formula:

wherein R^(1A) and R^(1B) are independently hydrogen, unsubstitutedC₁-C₈ alkyl, unsubstituted cycloalkyl, unsubstituted heterocycloalkyl,unsubstituted aryl, unsubstituted heteroaryl, C₁-C₆ alkylamine or

R² and R³ are independently hydrogen or unsubstituted C₁-C₂ alkyl; n isan integer from 1 to 30; and m is an integer from 1 to
 30. 21. A heavycrude oil emulsion comprising an amphiphilic co-solvent, a first phaseand a second phase, wherein said first phase comprises an oil-immisciblecompound and said second phase comprises a heavy crude oil; wherein saidamphiphilic co-solvent is an alkylamine or a compound having theformula:

wherein R^(1A) and R^(1B) are independently hydrogen, unsubstitutedC₁-C₈ alkyl, unsubstituted cycloalkyl, unsubstituted heterocycloalkyl,unsubstituted aryl, unsubstituted heteroaryl, C₁-C₆ alkylamine or

R² and R³ are independently hydrogen or unsubstituted C₁-C₂ alkyl; n isan integer from 1 to 30; and m is an integer from 1 to
 30. 22. The heavycrude oil emulsion of claim 21, wherein said heavy crude oil emulsiondoes not comprise water.
 23. The heavy crude oil emulsion of claim 21,wherein said amphiphilic co-solvent is present in said first phase andsaid second phase.
 24. A method of forming a heavy crude oil emulsion,said method comprising: (i) contacting a heavy crude oil extracted froman oil reservoir with an oil-immiscible compound and an amphiphilicco-solvent at an emulsion forming temperature, thereby forming a hightemperature heavy crude oil emulsion; (ii) allowing said hightemperature heavy crude oil emulsion to cool to a transport temperature,thereby forming a heavy crude oil emulsion; wherein said amphiphilicco-solvent is an alkylamine or a compound having the formula:

wherein R^(1A) and R^(1B) are independently hydrogen, unsubstitutedC₁-C₈ alkyl, unsubstituted cycloalkyl, unsubstituted heterocycloalkyl,unsubstituted aryl, unsubstituted heteroaryl, C₁-C₆ alkylamine or

R² and R³ are independently hydrogen or unsubstituted C₁-C₂ alkyl; n isan integer from 1 to 30; and m is an integer from 1 to
 30. 25. A methodof transporting an extracted heavy crude oil from a production well,comprising: (i) contacting an extracted heavy crude oil in a productionwell with an oil-immiscible compound, and an amphiphilic co-solvent atan emulsion forming temperature, thereby forming a heavy crude oilemulsion in a production well; (ii) transporting said heavy crude oilemulsion from said production well to the surface, thereby transportingsaid extracted heavy crude oil from said production well; wherein saidamphiphilic co-solvent is an alkylamine or a compound having theformula:

wherein R^(1A) and R^(1B) are independently hydrogen, unsubstitutedC₁-C₈ alkyl, unsubstituted cycloalkyl, unsubstituted heterocycloalkyl,unsubstituted aryl, unsubstituted heteroaryl, C₁-C₆ alkylamine or

R² and R³ are independently hydrogen or unsubstituted C₁-C₂ alkyl; n isan integer from 1 to 30; and m is an integer from 1 to 30.